Triethylamine → 2-Amino-3-benzoyl-5-chloro-α-(methylthio)benzeneacetamide
Reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].C(OCl)(C)(C)C.[CH3:23][S:24][CH2:25][C:26]([NH2:28])=[O:27].C(N(CC)CC)C>C(Cl)Cl>[NH2:1][C:2]1[C:3]([C:4](=[O:5])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[CH:12][C:13]([Cl:16])=[CH:14][C:15]=1[CH:25]([S:24][CH3:23])[C:26]([NH2:28])=[O:27]Participants
Procedure
To a cold (-70° C.) solution of 12.77 g (0.055 mole) of 2-amino-5-chlorobenzophenone in 300 mL of methylene chloride, under nitrogen atmosphere, was added 6.0 g (0.552 mole) of t-butylhypochlorite in 20 mL of methylene chloride. After the reaction was stirred for an additional 15 min, a suspension of 5.8 g (0.055 mole) of α-(methylthio)acetamide in 150 mL of methylene chloride was added. The mixture was stirred at -65° C. for 1 h. Triethylamine (5.6 g, 0.055 mole) was added and the solution was allowed to warm to room temperature. The reaction mixture was extracted with water and the organic layer dried over magnesium sulfate. The volume of the solution was reduced in vacuo to about 200 mL and the product crystallized as a yellow solid, m.p. 173.5°-174.5° C. Yield was 6.86 g (37.3%).
Workup
- additionwas added
- stirringThe mixture was stirred at -65° C. for 1 h
- extractionThe reaction mixture was extracted with water
- dry with materialthe organic layer dried over magnesium sulfate
- customthe product crystallized as a yellow solid, m.p. 173.5°-174.5° C
Sources & evidence
- ORD record
- ord-a425f2e364eb4008be119daaabf0d083
- Source dataset
- uspto-grants-1995_12
- Patent number
- US05475034
Reaction notes
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