Imidazole → HCID 131724300, compound

HRID 1840346Notes

Reaction equation

HRID 1840346 reaction equation
C1(NC(N)=S)C=CC=CC=1.[Cl:11][C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[NH:19][C:20]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([S:30]([NH:33][CH:34]2[CH2:38][CH2:37][O:36][NH:35]2)(=[O:32])=[O:31])[C:24]=1[OH:39])=[S:21].[Si:40](Cl)([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41].N1C=CN=C1>>[Cl:11][C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[NH:19][C:20]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([S:30]([NH:33][CH:34]2[CH2:38][CH2:37][O:36][NH:35]2)(=[O:31])=[O:32])[C:24]=1[O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])=[S:21]

Participants

5

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 676454PhenylthioureaHCID 131724301HCID 131724301, compound

Product 1

HCID 131724300HCID 131724300, compoundYield 49.3%

Procedure

Following the general procedure for protected phenyl thiourea formation outlined in example 1, N-(2,3-dichlorophenyl)-N′-[4-chloro-2-hydroxy-3-(N″-tetrahydroisoxazylaminosulfonyl)phenyl]thiourea (898 mg, 1.81 mmol), tert-butyldimethylsilyl chloride (1.4 g, 9.05 mmol) and imidazole (246 mg, 3.62 mmol) were reacted to form the desired product (546 mg, 49%). EI-MS m/z 611.81 (M+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-c2b2e855adf347549ec9b08aebbe2887
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

Loading…