Hydrochloric Acid → N-[p-bis(beta-chloroethyl)aminophenyl]-N'-(beta'-chloroethyl)urea
Reaction equation
[Cl:1][CH2:2][CH2:3][NH2:4].Cl.C(N(CCCC)CCCC)CCC.[Cl:19][CH2:20][CH2:21][N:22]([CH2:32][CH2:33][Cl:34])[C:23]1[CH:28]=[CH:27][C:26]([N:29]=[C:30]=[O:31])=[CH:25][CH:24]=1>CCOCC.CN(C)C=O.CCCCCC>[Cl:19][CH2:20][CH2:21][N:22]([CH2:32][CH2:33][Cl:34])[C:23]1[CH:24]=[CH:25][C:26]([NH:29][C:30]([NH:4][CH2:3][CH2:2][Cl:1])=[O:31])=[CH:27][CH:28]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 34 °C
Procedure
A mixture of β-chloroethylamine.HCl (5.80 g, 0.05 mole), hexane (60 ml), N,N-dimethylformamide (30 ml) and tributylamine (14.83 g; 0.08 mole) was cooled to -10° C., and an ether solution (100 ml) of p-bis(β-chloroethyl)aminophenyl isocyanate (12.9 g; 0.05 mole) was added with stirring. One hour later, the reaction mixture was heated at 34° C. for 6 hours. Low-boiling fractions were removed by distillation under reduced pressure. The residue was poured into ice water (500 ml), and the resulting white solid was collected by filtration and dried to give N-[p-bis(β-chloroethyl)aminophenyl]-N'-(β'-chloroethyl)urea (14.61 g). The yield was 86.3%.
Workup
- customLow-boiling fractions were removed by distillation under reduced pressure
- additionThe residue was poured into ice water (500 ml)
- filtrationthe resulting white solid was collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-07a8cdab7d7e45a381cc72b5516a0644
- Source dataset
- uspto-grants-1989_02
- Patent number
- US04803223
Reaction notes
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