Water → HCID 14627816, compound

HRID 1030235Notes

Reaction equation

HRID 1030235 reaction equation
[C:1](=[S:19])([O:3][C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[C:7]([OH:14])=[C:6]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:5]=1)[NH2:2].Cl[CH2:21][C:22](=O)[CH3:23].O>C(O)(=O)C>[C:15]([C:6]1[CH:5]=[C:4]([O:3][C:1]2[S:19][CH:21]=[C:22]([CH3:23])[N:2]=2)[CH:9]=[C:8]([C:10]([CH3:11])([CH3:12])[CH3:13])[C:7]=1[OH:14])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 6571ChloroacetoneHCID 14627811HCID 14627811, compound

Product 1

HCID 14627816HCID 14627816, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

O-(3,5-Di-tert-butyl-4-hydroxyphenyl) thiocarbamate (1.5 g) and 1.3 g of chloroacetone were dissolved in 60 ml of acetic acid, and the solution was heated at 90°-100° C. for 15 hours. The reaction mixture was poured into water and extracted with dichloromethane. The organic layer was washed with saturated aqueous sodium bicarbonate solution and then with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated. The crude product obtained was purified by silica gel column chromatography (diethyl ether-hexane =1:4) to give 1.0 g of the desired compound as a colorless solid.

Workup

  1. temperaturethe solution was heated at 90°-100° C. for 15 hours
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  4. dry with materialwith saturated aqueous sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product obtained
  7. customwas purified by silica gel column chromatography (diethyl ether-hexane =1:4)

Sources & evidence

ORD record
ord-67d32c46176b45aaa49251f6e2924895
Source dataset
uspto-grants-1992_04
Patent number
US05104889

Reaction notes

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