Imidazole → HCID 87433036, compound

HRID 1840359Notes

Reaction equation

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

Participants

Reactant 4

HCID 795Imidazole

HCID 28928tert-Butyldimethylsilyl chloride

HCID 676454Phenylthiourea

HCID 23447744HCID 23447744, compound

Product 1

HCID 87433036HCID 87433036, compoundYield 45%

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-trifluoromethylphenyl)thiourea (416 mg, 1.0 mmol), tert-butyldimethylsilyl chloride (750 mg, 5.0 mmol) and imidazole (136 mg, 2.0 mmol) were reacted to form the desired product (250 mg, 45%). EI-MS m/z 568.0 (M+).

Workup

customwere reacted

Sources & evidence

ORD record: ord-ec117852fc5e4d16b6dea0c0f53625a7
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680317B2

Reaction notes

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