Imidazole → HCID 131724298, compound

HRID 1840345Notes

Reaction equation

HRID 1840345 reaction equation
C1(NC(N)=S)C=CC=CC=1.[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([S:29]([NH:32][CH:33]2[CH2:37][CH2:36][O:35][NH:34]2)(=[O:31])=[O:30])[C:23]=1[OH:38])=[S:20].[Si:39](Cl)([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40].N1C=CN=C1>>[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([S:29]([NH:32][CH:33]2[CH2:37][CH2:36][O:35][NH:34]2)(=[O:31])=[O:30])[C:23]=1[O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])=[S:20]

Participants

5

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 676454PhenylthioureaHCID 131724299HCID 131724299, compound

Product 1

HCID 131724298HCID 131724298, compoundYield 45.4%

Procedure

Following the general procedure for protected phenyl thiourea formation outlined in example 1, N-(2-bromophenyl)-N′-[4-chloro-2-hydroxy-3-(N″-tetrahydroisoxazylaminosulfonyl)phenyl]thiourea (627 mg, 1.24 mmol), tert-butyldimethylsilyl chloride (934 mg, 6.2 mmol) and imidazole (169 mg, 2.48 mmol) were reacted to form the desired product (350 mg, 45%). EI-MS m/z 622 (M+) .

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-5f11f4581148499cbcf3f3ecbe6548ca
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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