Copper-catalyzed tandem reaction of 2-haloaniline derivatives with tetraalkylthiuram disulfides: Selective synthesis of 2-aminobenzothiazoles

Synlett

Volumn , Issue 18, 2009, Pages 3032-3036

  Pi, Sha Sha ^a   Zhang, Xing Guo ^a   Tang, Ri Yuan ^a   Li, Jin Heng ^a  

^a WENZHOU UNIVERSITY   (China)

Author keywords

2 aminobenzothiazoles; 2 haloanilimine; Copper; Tandem reaction; Tetraalkyl?thiuram disulfides

Indexed keywords

2 AMINOBENZOTHIAZOLE DERIVATIVE; 2 BROMOANILINE DERIVATIVE; 2 CHLOROANILINE DERIVATIVE; 2 HALOANILINE DERIVATIVE; 2 IODOANILINE DERIVATIVE; ANILINE DERIVATIVE; BENZOTHIAZOLE DERIVATIVE; COPPER; DISULFIDE; TETRAALKYLTHIURAM DISULFIDE; UNCLASSIFIED DRUG;

ARTICLE; SYNTHESIS;

EID: 72049099630     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218276     Document Type: Article

References (42)

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42. General Procedure for the Copper-Catalyzed Tandem Reaction of 2-Haloanilimine Derivatives with Tetraalkylthiuram Disulfides A flame-dried Schlenk tube with a magnetic stirring bar was charged with 2-haloanilimine derivative 1 (0.2 mmol), tetraalkylthiuram disulfide (0.15 mmol), CuBr (1.4 mg, 0.01 mmol), Cs2CO3 (196 mg, 0.6 mmol), and DMSO (1 mL). The reaction mixture was stirred at 80 ?C for the indicated time (Tables 1 and 2) until complete consumption of starting material as monitored by TLC and GC-MS analysis. After the reaction was finished, the mixture was poured into EtOAc, washed with brine (3 ×10 mL), and extracted with EtOAc. The combined organic layers were dried over anhyd Na2SO4 and evaporated under vacuum. The residue was purified by flash column chromatography (hexane?EtOAc) to afford the desired product. N,N-Dimethy-6-(trifluoromethyl)benzo[d]thiazol-2-amine (4) Mp 98.5?101.1 ?C(uncorrected). 1H NMR (300 MHz, CDCl3): d = 7.84 (s, 1 H), 7.58 (d, J = 8.5 Hz, 1 H), 7.52 (d, J = 8.5 Hz, 1 H), 3.22 (s, 6 H). 13C NMR (75 MHz, CDCl3): d = 170.3, 155.8, 131.2, 124.6 (q, JC?F = 269.9 Hz, 1 C), 123.4, 122.8 (d, JC?F = 32.2 Hz, 1 C), 122.1, 118.0, 40.2. 19F NMR (283 MHz, CDCl3): d = ?60.79. IR (KBr): 2913, 1616, 1573, 1337, 1145, 1099 cm?1. LRMS (EI, 70 eV): m/z (%) = 246 (93) [M+], 217 (100). ESI-HRMS: m/z calcd for C10H10F3N2S+ [M + H]+: 247.0511; found: 247.0503.