Imidazole → HCID 178486147, compound

HRID 1840353Notes

Reaction equation

HRID 1840353 reaction equation
[C:1]1([NH:7]C(N)=S)C=CC=CC=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])=S)=[C:14]([OH:29])[C:13]=1[S:30]([N:33]([CH3:35])[CH3:34])(=[O:32])=[O:31].[Si](Cl)(C(C)(C)C)(C)C.[NH:44]1C=CN=C1>>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([C:1]#[N:7])[C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])=[NH:44])=[C:14]([OH:29])[C:13]=1[S:30]([N:33]([CH3:35])[CH3:34])(=[O:32])=[O:31]

Participants

5

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 676454PhenylthioureaHCID 23447787HCID 23447787, compound

Product 1

HCID 178486147HCID 178486147, compoundYield 49%

Procedure

Following the general procedure for protected phenyl thiourea formation outlined in example 12, N-[4-chloro-2-hydroxy-3-(N″,N″-dimethylaminosulfonyl)phenyl]-N′-(2-chlorophenyl)thiourea (500 mg, 1.19 mmol), tert-butyldimethylsilyl chloride (897 mg, 5.95 mmol) and imidazole (162 mg, 2.38 mmol) were reacted to form the desired product (311 mg, 49%). EI-MS m/z 535.32 (M+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-793c0ddf29f34afdb72e0efaea1ab409
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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