Cyclamate → 1-(1-n-Butyl-2-pyrrolidylidene)-3-(m-chlorophenyl)urea

HRID 1973935Notes

Reaction equation

HRID 1973935 reaction equation
C1(NS(=O)(=O)O)CCCCC1.[CH2:12]([N:16]1[CH2:20][CH2:19][CH2:18][C:17]1=[NH:21])[CH2:13][CH2:14][CH3:15].[Cl:22][C:23]1[CH:24]=[C:25]([N:29]=[C:30]=[O:31])[CH:26]=[CH:27][CH:28]=1>>[CH2:12]([N:16]1[CH2:20][CH2:19][CH2:18][C:17]1=[N:21][C:30]([NH:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([Cl:22])[CH:24]=1)=[O:31])[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 3

HCID 7533CyclamateHCID 17968Benzene, 1-chloro-3-isocyanato-HCID 124490221-n-Butyl-2-iminopyrrolidine

Product 1

HCID 545448951-(1-n-Butyl-2-pyrrolidylidene)-3-(m-chlorophenyl)urea

Procedure

The cyclohexylsulfamic acid salt of 1-n-butyl-2-iminopyrrolidine (15.97 g.; 0.05 mole) is converted to free base (7.01 g.; 0.05 mole) in the usual manner. After drying over K2CO3, the benzene solution is filtered through diatomaceous earth and 7.68 g. (0.05 mole) of m-chlorophenylisocyanate is added. The reaction mixture is stirred at room temperature for 21/2 hours and then taken to dryness in vacuo leaving a solid residue, 1-(1 -n-butyl2-pyrrolidylidene)-3-(m-chlorophenyl)urea. Recrystallizations from ethyl acetate yields the pure product, m.p. = 94-96° C.

Workup

  1. dry with materialAfter drying over K2CO3
  2. filtrationthe benzene solution is filtered through diatomaceous earth and 7.68 g

Sources & evidence

ORD record
ord-842f64eff6df4e48ac81a8e827ed1d2b
Source dataset
uspto-grants-1976_12
Patent number
US03998958

Reaction notes

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