2-Chloroacrylonitrile → HCID 21711804, compound

HRID 651247Notes

Reaction equation

HRID 651247 reaction equation
[N:1]([CH:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[NH:6][C:5]1=[O:15])=[N+:2]=[N-:3].Cl[C:17](=[CH2:20])[C:18]#[N:19]>O>[C:18]([C:17]1[N:3]=[N:2][N:1]([CH:4]2[CH2:10][CH2:9][C:8]3[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=3[NH:6][C:5]2=[O:15])[CH:20]=1)#[N:19]

Participants

4

Reactant 2

HCID 701982-ChloroacrylonitrileHCID 109325203-Azido-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

Product 1

HCID 21711804HCID 21711804, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-azido-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine (1.01 g) and 2-chloroacrylonitrile (0.95 g) in water (5 ml) is stirred at about 80° C. for 18 hours. Excess 2-chloroacrylonitrile is distilled off in vacuo, and the precipitated product is filtered off, washed with water and dried (yield 1.1 g; 87% of theory), m.p. 214-216° C. (recrystallization from ethyl acetate/toluene).

Workup

  1. distillationExcess 2-chloroacrylonitrile is distilled off in vacuo
  2. filtrationthe precipitated product is filtered off
  3. washwashed with water
  4. customdried
  5. custom(yield 1.1 g; 87% of theory), m.p. 214-216° C. (recrystallization from ethyl acetate/toluene)

Sources & evidence

ORD record
ord-d510fa2bebd14e89b7752766e94a7a14
Source dataset
uspto-grants-2001_08
Patent number
US06277999B1

Reaction notes

Loading…