Triethylamine → HCID 53849556, compound

HRID 2259722Notes

Reaction equation

HRID 2259722 reaction equation
NC1C=CC=CC=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)=[O:5].C(OCl)(C)(C)C.[CH3:23][S:24][CH2:25][C:26]([NH:28][CH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[C:34]([O:40][CH3:41])[CH:33]=1)=[O:27].C([N:44](CC)CC)C>C(Cl)Cl>[NH2:44][CH:25]([S:24][CH3:23])[C:26]([NH:28][CH2:29][CH2:30][CH:31]([C:4](=[O:5])[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[C:34]([O:40][CH3:41])[CH:33]=1)=[O:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 521297Tert-Butyl hypochloriteHCID 98372872-Amino-4'-fluorobenzophenoneHCID 19001717HCID 19001717, compound

Product 1

HCID 53849556HCID 53849556, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 21.5 g (0.1 mole) of 2-amino- 4'-fluoro-benzophenone in 400 mL of methylene chloride, cooled to -70° C. is added 11.5 g (0.1 mole) of 95% t-butylhypochlorite over 15 min, keeping the temperature below -66° C. To this solution is added a solution of α-(methylthio)-N-3-(3,4-dimethoxyphenyl)propylacetamide (0.1 mole) in 50 mL of methylene chloride over a ten minute period. The solution is stirred for 1 h at -65° to -70° C. and then is allowed to warm to 0° C. Triethylamine (0.1 mole) is added and the resulting solution is washed with water. The organic solution is dried with magnesium sulfate, and concentrated in vacuo. The product is isolated using standard conditions.

Workup

  1. customthe temperature below -66° C
  2. washthe resulting solution is washed with water
  3. dry with materialThe organic solution is dried with magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe product is isolated

Sources & evidence

ORD record
ord-979d5c746cf844e89ed0ccf43a715baa
Source dataset
uspto-grants-1995_12
Patent number
US05475034

Reaction notes

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