2-Chloroacrylonitrile → HCID 57065490, compound

HRID 651249Notes

Reaction equation

HRID 651249 reaction equation
[N:1]([C@@H:4]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:2]=[N-:3].Cl[C:19](=[CH2:22])[C:20]#[N:21]>O>[C:20]([C:19]1[N:3]=[N:2][N:1]([C@@H:4]([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:22]=1)#[N:21]

Participants

4

Reactant 2

HCID 701982-ChloroacrylonitrileHCID 12024357HCID 12024357, compound

Product 1

HCID 57065490HCID 57065490, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 2-azido-4-phenyl-(2S)-butyrate (2.33 g) and 2-chloroacrylonitrile (1.75 g) in water (25 ml) is stirred at about 80° C. for 23 hours. After cooling, the product is extracted with toluene and purified by column chromatography (30 g of silica gel 60; eluent toluene). The purified product is obtained as a yellowish oil (yield 1.84 g; 65% of theory) and characterized by 1H-NMR spectrum (CDCl3). δ value: 1.29 (*H; t; J=7 Hz); 2.40-2.67 (4H, m); 4.20 (2H, q, J=7 Hz); 5.39 (1H, m); 7.10 (2H, dxd, J1=6.6 Hz, J2≦1.5 Hz); 7.24 (1H, txt, J1=6.6 Hz, J2≦1.5 Hz); 7.31 (2h, m); 8.21 (1H, s).

Workup

  1. temperatureAfter cooling
  2. extractionthe product is extracted with toluene
  3. custompurified by column chromatography (30 g of silica gel 60; eluent toluene)
  4. customThe purified product is obtained as a yellowish oil (yield 1.84 g; 65% of theory)

Sources & evidence

ORD record
ord-8b13b33f2abc4b57ab00d275ca68ebc1
Source dataset
uspto-grants-2001_08
Patent number
US06277999B1

Reaction notes

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