2-Chloroethyl isocyanate → HCID 23301804, compound

HRID 1952986Notes

Reaction equation

HRID 1952986 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1)#[N:2].[Cl:11][CH2:12][CH2:13][N:14]=[C:15]=[O:16]>>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:15]([NH:14][CH2:13][CH2:12][Cl:11])=[O:16])=[CH:5][CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 826084-(Aminomethyl)benzonitrile

Product 1

HCID 23301804HCID 23301804, compound

Procedure

The 4-cyanobenzenemethanamine obtainable by modified Gabriel synthesis, when reacted with chloroethylisocyanate, yields 1-[(4-cyanophenyl)methyl]-3-(2-chloroethyl)urea which when treated with potassium tert.butoxide in dimethylformamide is easily cyclised into the 1-[(4-cyanophenyl)methyl]-2-imidazo-lidinone; catalytic hydrogenation then leads to the desired 4-[(2-oxo-1-imidazolidinyl)methyl]benzenemethanamine.

Workup

  1. customGabriel synthesis, when

Sources & evidence

ORD record
ord-e9b4112477a74ecc92c24b840ff933b5
Source dataset
uspto-grants-2000_09
Patent number
US06114390

Reaction notes

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