Imidazole → N-(4-cyano-2-t-butyldimethylsilanoxyphenyl)-N'-(2-bromophenyl)thio urea

HRID 413342Notes

Reaction equation

HRID 413342 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Br:19])=[S:11])=[C:5]([OH:20])[CH:4]=1)#[N:2].N1C=CN=C1.[CH3:26][C:27]([Si:30](Cl)([CH3:32])[CH3:31])([CH3:29])[CH3:28]>C1COCC1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Br:19])=[S:11])=[C:5]([O:20][Si:30]([C:27]([CH3:29])([CH3:28])[CH3:26])([CH3:32])[CH3:31])[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 12043084N-(4-cyano-2-hydroxyphenyl)-N'-(2-bromophenyl) thiourea

Product 1

HCID 12043082N-(4-cyano-2-t-butyldimethylsilanoxyphenyl)-N'-(2-bromophenyl)thio ureaYield 84.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(4-cyano-2-hydroxyphenyl)-N′-(2-bromophenyl)thio urea (3.5 g, 10 mmol) in THF (50 mL) at 0° C. was added imidazole (1.0 g, 15 mmol) and TBSCl (1.5 g, 10 mmol). After 1 h, the reaction mixture quenched with water (100 mL) and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude material was crystallized from ethyl acetate to give 3.9 g (84%) of N-(4-cyano-2-t-butyldimethylsilanoxyphenyl)-N′-(2-bromophenyl)thio urea as a yellow solid. 1H NMR (400 MHz, DMSO) δ 9.9 (s, 1H), 9.2 (s, 1H), 8.1 (d, 1H), 7.7 (d, 1H), 7.6 (d, 1H), 7.45 (d, 1H), 7.4 (t, 1H), 7.35 (s, 1H), 7.2 (t, 1H); MS(EI) m/e 347 (100 (M+)), 175 (40), 461 (40).

Workup

  1. customthe reaction mixture quenched with water (100 mL)
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-a4da80806b9241498622a317474c76bd
Source dataset
uspto-grants-2003_05
Patent number
US06566387B1

Reaction notes

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