N,N-Dimethylaniline → HCID 22716515, compound

HRID 1582938Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[S:9][CH2:10][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[N:12]=1.CN(C)C1C=CC=CC=1.Cl[C:30]([N:32]=[C:33]=[O:34])=[O:31].[Cl:35][CH2:36]Cl>>[Cl:35][C:36]1[CH:2]=[CH:7][CH:6]=[CH:5][C:4]=1[C:3]1[C:30](=[O:31])[NH:32][C:33](=[O:34])[N:12]2[CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[CH2:10][S:9][C:8]=12

Participants

Reactant 4

HCID 949N,N-Dimethylaniline

HCID 6344Dichloromethane

HCID 119708Isocyanatocarbonyl chloride

HCID 22716548HCID 22716548, compound

Product 1

HCID 22716515HCID 22716515, compoundYield 67%

Procedure

To 2-(2-chlorophenyl)-4-(2-fluorophenyl)-4,5-dihydrothiazole (0.303 g, 1.00 mmol) and N,N-dimethylaniline (0.135 mL, 1.05 mmol) in dichloromethane (2 mL) at 0° C. was added dropwise chlorocarbonyl isocyanate (0.080 mL, 1.0 mmol). The mixture was allowed to warm to room temperature and stirred for 24 hours. The resulting suspension was cooled to 0° C., filtered, and washed with ice-cold 1:1 dichloromethane/ether (2×1 mL) to give the title compound as a white powder (0.251 g, 67%). MS=375.1 ((M+H)+). 1H NMR (TMS/DMSO-D6, 400 MHz): 7.59-7.08 (m, 8H); 6.18 (d, J=7.6 Hz, 1H); 4.05 (dd, J=11.2, 7.6 Hz, 1H); 3.25 (d, J=11.2, 1H); 2.87 (s, 1H).

Workup

temperatureThe resulting suspension was cooled to 0° C.
filtrationfiltered
washwashed with ice-cold 1:1 dichloromethane/ether (2×1 mL)

Sources & evidence

ORD record: ord-e36f33669d59407ba031e17a4ada9a5a
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06740656B2

Reaction notes

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