Imidazole → HCID 23447742, compound

HRID 1840366Notes

Reaction equation

HRID 1840366 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[F:28])=[S:20])=[C:14]([OH:29])[C:13]=1[S:30]([N:33]([CH3:35])[CH3:34])(=[O:32])=[O:31].[Si:36](Cl)([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37].N1C=CN=C1>>[F:28][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:30]([N:33]([CH3:35])[CH3:34])(=[O:31])=[O:32])[C:14]=1[O:29][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])=[S:20]

Participants

5

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 676454PhenylthioureaHCID 23447840HCID 23447840, compound

Product 1

HCID 23447742HCID 23447742, compoundYield 69%

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-fluorophenyl)thiourea (440 mg, 1.09 mmol), tert-butyldimethylsilyl chloride (817 mg, 5.45 mmol) and imidazole (148 mg, 2.18 mmol) were reacted to form the desired product (387 mg, 69%). EI-MS m/z 518.2 (M+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-cce430d25bda4fbdba778171c5be00f4
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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