(5-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)methanol → HCID 69686671, compound

HRID 1005546

Reaction equation

HRID 1005546 reaction equation
[OH:1][CH2:2][C:3]1[N:4]([CH2:20][CH3:21])[C:5]([S:11][C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=2)=[C:6]([CH:8]([CH3:10])[CH3:9])[N:7]=1.[C:22]([N:28]=[C:29]=[O:30])(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24]>O1CCCC1>[C:22]([NH:28][C:29](=[O:30])[O:1][CH2:2][C:3]1[N:4]([CH2:20][CH3:21])[C:5]([S:11][C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=2)=[C:6]([CH:8]([CH3:9])[CH3:10])[N:7]=1)(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 473933(5-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)methanolHCID 126188362,2-dimethylpropanecarbonyl isocyanate

Product 1

HCID 69686671HCID 69686671, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound 19 (200 mg, 0.580 mmol) in tetrahydrofuran (1 mL) under ice-cooling was added pivaloyl isocyanate (5 eq.), and stirred at the same temperature for 1 hour. After removing condenser, the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was partitioned between ethyl acetate and phosphate buffer (pH 7.0). The organic layer was separated, washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (eluate: hexane - ether (2:1)) to give the compound 81 (227 mg, 83%) as crystals. Mp. 157-159° C. Rf 0.31 (1:2 EtOAc-hexane).

Workup

  1. customAfter removing condenser
  2. stirringthe reaction mixture was stirred at room temperature for 1 hour
  3. customThe reaction mixture was partitioned between ethyl acetate and phosphate buffer (pH 7.0)
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on a silica gel column (eluate: hexane - ether (2:1))

Sources & evidence

ORD record
ord-4895766e87fa4d9a921499ecd7f2a58c
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Linked notes

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