Imidazole → HCID 15095371, compound

HRID 2083858Notes

Reaction equation

HRID 2083858 reaction equation
[C:1](Cl)(Cl)=[S:2].N1C=CN=C1.[CH2:10]([CH:13]1[CH2:18][CH2:17][CH:16]([CH:19]2[CH2:24][CH2:23][CH:22]([C:25]3[CH:30]=[C:29]([F:31])[C:28]([NH2:32])=[C:27]([F:33])[CH:26]=3)[CH2:21][CH2:20]2)[CH2:15][CH2:14]1)[CH2:11][CH3:12]>ClCCl>[F:31][C:29]1[CH:30]=[C:25]([CH:22]2[CH2:21][CH2:20][CH:19]([CH:16]3[CH2:17][CH2:18][CH:13]([CH2:10][CH2:11][CH3:12])[CH2:14][CH2:15]3)[CH2:24][CH2:23]2)[CH:26]=[C:27]([F:33])[C:28]=1[N:32]=[C:1]=[S:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 10040ThiophosgeneHCID 22731669HCID 22731669, compound

Product 1

HCID 15095371HCID 15095371, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.9 ml of thiophosgene are added dropwise over the course of 30 minutes at 15-25° C. to 18.4 g of imidazole in 150 ml of dichloromethane, and the mixture is stirred at RT for a further 2 hours. 15.8 g of 4-(4′-n-propylbicyclohexyl-4-yl)-2,6-difluorophenylamine (prepared as described in Examples 1a-1e) are subsequently added, and the mixture is stirred at RT for 24 hours. Conventional work-up gives 4′-(3,5-difluoro-4-isothiocyanatophenyl)-4-n-propylbicyclohexyl having the following properties: C 65 N 225.5 1; Δε 16.0; Δn 0.1990.

Workup

  1. stirringthe mixture is stirred at RT for 24 hours

Sources & evidence

ORD record
ord-79e5e99ff7524cba8159a210af91f2c3
Source dataset
uspto-grants-2004_04
Patent number
US06716491B2

Reaction notes

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