Imidazole → N-[4-Chloro2-tert-butyldimethylsilyloxy-3-(N'',N''-dimethylaminosulfonyl)phenyl]-N'-(2,3-dichlorophenyl)thiourea

HRID 1840338Notes

Reaction equation

HRID 1840338 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]=[C:14]([Cl:18])[C:13]=2[Cl:19])=[S:10])=[C:4]([OH:20])[C:3]=1[S:21]([N:24]([CH3:26])[CH3:25])(=[O:23])=[O:22].[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].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]=[C:14]([Cl:18])[C:13]=2[Cl:19])=[S:10])=[C:4]([O:20][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[C:3]=1[S:21]([N:24]([CH3:26])[CH3:25])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 10297913N-[4-Chloro-2-hydroxy-3[N'',N''-dimethylaminosulfonyl]phenyl]-N'-(2,3-dichlorophenyl)thiourea

Product 1

HCID 23447765N-[4-Chloro2-tert-butyldimethylsilyloxy-3-(N'',N''-dimethylaminosulfonyl)phenyl]-N'-(2,3-dichlorophenyl)thioureaYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[4-chloro-2-hydroxy-3-(N″,N″-dimethylaminosulfonyl)phenyl]-N′-(2,3dichlorophenyl)thiourea (440 mg, 1.07 mmol) in THF (20 mL), tert-butyldimethylsilyl chloride (730 mg, 4.85 mmol) and imidazole (132 mg, 1.94 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 (270 mg, 50%). EI-MS m/z 570 (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-25abe7e906a74eb59399af693a1ab546
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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