Ethyl Acetate → HCID 21465922, compound

HRID 1940194Notes

Reaction equation

HRID 1940194 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:11](=[O:23])[CH2:10][CH2:9]1.[Cl:24]N1C(=O)CCC1=O.C(OC(=O)C)C>CN(C)C=O>[Cl:24][C:16]1[CH:17]=[CH:18][C:13]2[N:12]([CH2:19][CH:20]([CH3:21])[CH3:22])[C:11](=[O:23])[CH2:10][CH2:9][CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:14]=2[CH:15]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 31398ChlorosuccinimideHCID 21465915HCID 21465915, compound

Product 1

HCID 21465922HCID 21465922, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(2-chlorophenyl)-1-isobutyl-2,3,4,5-tetrahydro-1H-[1]-benzazepin-2-one (2.7 g) and N-chlorosuccinimide (1.65 g) in dimethylformamide (10 ml) was stirred for 7 hours at 70° C. To the reaction mixture was added acetic acid ethyl ester (100 ml), which was washed with dilute hydrochloric acid and a saturated aqueous solution of sodium hydrogencarbonate, followed by drying over anhydrous sodium sulfate. The solvent was removed, and the residue was recrystallized from hexane/acetic acid ethyl ester to give 2.39 g of colorless crystals, m.p. 152°-154° C.

Workup

  1. washwas washed with dilute hydrochloric acid
  2. dry with materialby drying over anhydrous sodium sulfate
  3. customThe solvent was removed
  4. customthe residue was recrystallized from hexane/acetic acid ethyl ester

Sources & evidence

ORD record
ord-341cd8842aea46f489ce8d2390744a41
Source dataset
uspto-grants-1997_12
Patent number
US05698691

Reaction notes

Loading…