Simple preparation of monoalkylhydrazines

Synlett

Volumn , Issue 13, 2004, Pages 2355-2356

  Meyer, Kevin G ^a  

^a DOW AGROSCIENCES LLC   (United States)

Author keywords

Acid hydrolysis; Alkylation; Hydrazine; Phase transfer; t butyl carbazate

Indexed keywords

BROMINE DERIVATIVE; CARBAZIC ACID DERIVATIVE; HYDRAZINE DERIVATIVE; TERT BUTYL ISOPROPYLIDENE CARBAZATE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; HYDROLYSIS; PHASE TRANSITION; REACTION ANALYSIS; SYNTHESIS;

EID: 8644279653     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-831336     Document Type: Article

References (16)

1. Kabalka, G. W.; Guchhait, S. K. Org. Lett. 2003, 5, 4129.
2. (a) Zawadzki, S.; Zwierzak, A. Polish J. Chem. 2003, 77, 315.
3. (b) Tšubrik, O.; Mäeorg, U.; Ragnarsson, U. Tetrahedron Lett. 2002, 6213.
4. (c) Tšubrik, O.; Mäeorg, U. Org. Lett. 2001, 3, 2297.
5. (a) Smith, P. A. S. The Chemistry of Open Chain Nitrogen Compounds, Vol. 2; W. A. Benjamin: New York, 1966, Chap. 9.
6. (b) Sidgwick, N. V. Organic Chemistry of Nitrogen, 3rd ed.; Oxford University Press: London, 1966, Chap. 15.
7. (c) Timberlake, J. W.; Stowell, J. C. In Chemistry of Hydrazo-, Azo-, and Azoxy Groups; Patai, S., Ed.; Wiley: New York, 1975, Chap. 4.
8. Ghali, N. I.; Venton, D. L.; Hung, S. C.; Le Breton, G. C. J. Org. Chem. 1981, 46, 5413.
9. Zawadski, S.; Osowska-Pacewicka, K.; Zwierzak, A. Synth. Commun. 1987, 485.
10. The alkylation conditions described in ref.5 have also been used for N-alkylation of N-substitued carboxamides. See: Koziara, A.; Zawadzki, S.; Zwierzak, A. Synth. Commun. 1979, 527.
11. Hydrazine 3e was prepared on 1 mol scale (68% overall yield) without any modification of the experimental procedure. In addition, a differential scanning calorimetry (DSC) test established compound 1 to be chemically stable in the temperature range described in the reaction conditions.
12. Alkylations with allyl and benzyl chlorides were performed under identical conditions as those described for alkyl bromides with comparable yields and purities.
13. The stock solutions of hydrazines have been stored in amber vials at room temperature for up to 1 year with no noticeable loss of molarity.
14. 3): δ = 16.1, 25.5, 28.4, 81.0, 150.0, 153.1.
15. 3): δ = 7.29 (m, 5 H), 4.68 (s, 2 H), 2.03 (s, 3 H), 1.70 (s, 3 H), 1.45 (s, 9 H).
16. 6-DMSO): δ = 54.3, 128.8, 129.1, 130.1, 134.6.