Chloroacetyl isocyanate → HCID 21161936, compound

HRID 893957Notes

Reaction equation

HRID 893957 reaction equation
[C:1]([CH:3]1[CH:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:4]1)#[N:2].[Cl:12][CH2:13][C:14]([N:16]=[C:17]=[O:18])=[O:15]>C(OCC)C>[Cl:12][CH2:13][C:14]([NH:16][C:17]([N:4]1[CH:5]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:3]1[C:1]#[N:2])=[O:18])=[O:15]

Participants

4

Reactant 2

HCID 78209Chloroacetyl isocyanateHCID 13181976HCID 13181976, compound

Product 1

HCID 21161936HCID 21161936, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

1 g. Crude 2-cyano-3-phenyl-aziridine is dissolved in 25 ml. anhydrous diethyl ether. A solution of 0.83 g. chloroacetyl isocyanate in 3.5 ml. diethyl ether is added thereto dropwise, while stirring, and the reaction mixture is further stirred for 1 hour at ambient temperature. The precipitate obtained is then filtered off with suction, washed with diethyl ether and dried in a vacuum. There is thus obtained 1.24 g. 1-(N-chloroacetyl-carbamoyl)-2-cyano3-phenyl-aziridine; m.p. 153°-158°-165° C. According to the NMR spectrum, the product is an isomeric mixture containing about 30% of the trans form and about 70% of the cis form.

Workup

  1. stirringthe reaction mixture is further stirred for 1 hour at ambient temperature
  2. customThe precipitate obtained
  3. filtrationis then filtered off with suction
  4. washwashed with diethyl ether
  5. customdried in a vacuum
  6. customm.p. 153°-158°-165° C
  7. additioncontaining about 30% of the trans form and about 70% of the cis form

Sources & evidence

ORD record
ord-c66b503488bc465190041140cab1fb7d
Source dataset
uspto-grants-1981_08
Patent number
US04282212

Reaction notes

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