Imidazole → N-[4-Chloro-2-tert-butyldimethylsilyloxy-3-(N'',N''-dimethylaminosulfonyl)phenyl]-N'-(2-bromophenyl)thiourea

HRID 1840337Notes

Reaction equation

HRID 1840337 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Br:18])=[S:10])=[C:4]([OH:19])[C:3]=1[S:20]([N:23]([CH3:25])[CH3:24])(=[O:22])=[O:21].[Si:26](Cl)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27].N1C=CN=C1>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Br:18])=[S:10])=[C:4]([O:19][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[C:3]=1[S:20]([N:23]([CH3:25])[CH3:24])(=[O:21])=[O:22]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 10183328N-[4-Chloro-2-hydroxy-3-[N'',N''-dimethylaminosulfonyl]phenyl]-N'-(2-bromophenyl)thiourea

Product 1

HCID 23447779N-[4-Chloro-2-tert-butyldimethylsilyloxy-3-(N'',N''-dimethylaminosulfonyl)phenyl]-N'-(2-bromophenyl)thioureaYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[4-chloro-2-hydroxy-3-(N″,N″-dimethylaminosulfonyl)phenyl]-N′-(2-bromophenyl)thiourea (500 mg, 1.07 mmol) in THF (20 mL), tert-butyldimethylsilyl chloride (810 mg, 5.35 mmol) and imidazole (144 mg, 2.14 mmol) were added. The reaction mixture was stirred at room temperature for 16 hours. Then it was partitioned between ethyl acetate and water. The combined organic phase was dried and concentrated. Chromatography of the residue on silica gel (30% Ethyl acetate/Hexane) gave desired product (240 mg, 40%) and recovered starting material (280 mg). EI-MS m/z 580 (M+).

Workup

  1. customThen it was partitioned between ethyl acetate and water
  2. customThe combined organic phase was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4eb555a94fac484b81f0b9c604fdfcff
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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