Imidazole → HCID 23447795, compound

HRID 1840382Notes

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]=[C:24]([F:28])[C:23]=2[Cl:29])=[S:20])=[C:14]([OH:30])[C:13]=1[S:31]([N:34]([CH3:36])[CH3:35])(=[O:33])=[O:32].[Si:37](Cl)([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38].N1C=CN=C1>>[Cl:29][C:23]1[C:24]([F:28])=[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:31]([N:34]([CH3:36])[CH3:35])(=[O:33])=[O:32])[C:14]=1[O:30][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])=[S:20]

Participants

Reactant 4

HCID 795Imidazole

HCID 28928tert-Butyldimethylsilyl chloride

HCID 676454Phenylthiourea

HCID 23447736HCID 23447736, compound

Product 1

HCID 23447795HCID 23447795, compoundYield 50.3%

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-chloro-3-fluorophenyl)thiourea (575 mg, 1.32 mmol), tert-butyldimethylsilyl chloride (991 mg, 6.6 mmol) and imidazole (179 mg, 2.64 mmol) were reacted to form the desired product (367 mg, 50%). LC-MS m/z 552.2 (M+).

Workup

customwere reacted

Sources & evidence

ORD record: ord-b56eca2aadff49079347ca6ca515ac39
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680317B2

Reaction notes

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