Triethylamine → HCID 20552976, compound

HRID 1446818Notes

Reaction equation

HRID 1446818 reaction equation
N[C:2]1C=C[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:17]([O:21]Cl)(C)(C)C.[CH3:23][S:24][CH2:25][C:26]([NH2:28])=O.C([N:31](CC)CC)C>C(Cl)Cl>[NH2:28][CH:26]([CH:25]([S:24][CH3:23])[CH2:2][CH:3]([C:4](=[O:5])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:12][CH2:13][Cl:16])[C:17]([NH2:31])=[O:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 128702-Amino-5-chlorobenzophenoneHCID 521297Tert-Butyl hypochloriteHCID 5478732-(Methylthio)acetamide

Product 1

HCID 20552976HCID 20552976, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

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 an additional 15 min stirring period, 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 one hour. 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 several portions of water and the organic layer dried over magnesium sulfate. The volume of 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

  1. additionwas added
  2. stirringThe mixture was stirred at -65° C. for one hour
  3. extractionThe reaction mixture was extracted with several portions of water
  4. dry with materialthe organic layer dried over magnesium sulfate
  5. customthe product crystallized as a yellow solid, m.p. 173.5°-174.5° C

Sources & evidence

ORD record
ord-c51f68dae0ce4062b2c159eb15e08e9c
Source dataset
uspto-grants-1982_02
Patent number
US04313949

Reaction notes

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