Water → HCID 12535975, compound

HRID 224344Notes

Reaction equation

HRID 224344 reaction equation
[C:1]1([CH:7]2[CH2:13][C:12](=[O:14])[NH:11][C:10]3[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=3[S:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:19]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:19][C:13]1[C:12](=[O:14])[NH:11][C:10]2[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=2[S:8][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 38949029476-22-0

Product 1

HCID 12535975HCID 12535975, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A stirred solution of 25.5 g (0.1 mole) of 2,3-dihydro-2-phenyl-1,5-benzothiazepin-4(5H)-one (prepared as disclosed by Krapcho et al, J. Med. Chem., 6, 544, (1963)) in 250 ml of dimethylformamide is treated with a solution of 35 g (0.2 mole) of N-bromosuccinimide in 100 ml of dimethylformamide. The mixture is stirred at 105°-110° for 5 hours, cooled, and poured into 1.8 liters of cold H2O to precipitate a solid. After cooling overnight, the latter is filtered, washed with H2O, and air-dried; wt. 29.6 g (89%); m.p. 190°-192°; s. 180°. Following crystallization from a mixture of 30 ml of hot dimethylformamide and 60 ml of MeCN, the colorless solid weighs 17.8 g (53%); m.p. 240°-242° (dec.).

Workup

  1. temperaturecooled
  2. customto precipitate a solid
  3. temperatureAfter cooling overnight
  4. filtrationthe latter is filtered
  5. washwashed with H2O
  6. customair-dried
  7. custom180°
  8. customcrystallization
  9. additionfrom a mixture of 30 ml of hot dimethylformamide and 60 ml of MeCN

Sources & evidence

ORD record
ord-0d9bb25956ea4208a139d0754f3e1d94
Source dataset
uspto-grants-1980_11
Patent number
US04232027

Reaction notes

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