Chlorosuccinimide → HCID 14877443, compound

HRID 1608198Notes

Reaction equation

HRID 1608198 reaction equation
[C:1]([NH:4][C:5]1[CH:28]=[CH:27][C:8]([C:9]([NH:11][CH2:12][CH:13]2[O:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:14]2)=[O:10])=[C:7]([O:29][CH2:30][CH3:31])[CH:6]=1)(=[O:3])[CH3:2].[Cl:32]N1C(=O)CCC1=O>CN(C)C=O>[C:1]([NH:4][C:5]1[C:28]([Cl:32])=[CH:27][C:8]([C:9]([NH:11][CH2:12][CH:13]2[O:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:14]2)=[O:10])=[C:7]([O:29][CH2:30][CH3:31])[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 198486134-acetylamino-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl]methyl]benzamide

Product 1

HCID 14877443HCID 14877443, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 4-acetylamino-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl]methyl]benzamide (4.0 g) in dimethylformamide (20 ml) is N-chlorosuccinimide (1.3 g), and the resulting mixture is stirred at 70° C. for 2 hours. The reaction mixture is poured into ice-water and extracted with diethyl ether. The organic layer is washed successively with water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and evaporated. The residue is recrystallized from acetone to give the title compound (3.1 g), mp 161°-163° C.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic layer is washed successively with water and saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue is recrystallized from acetone

Sources & evidence

ORD record
ord-1e8140a0b9534a2ebdd94884d82e07b5
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

Loading…