Cyclamate → 1-(1-n-Butyl-2-pyrrolidylidene)-3-(2,6-dimethylphenyl)urea

HRID 2071504Notes

Reaction equation

HRID 2071504 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].[CH3:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:24]=1[N:30]=[C:31]=[O:32]>>[CH2:12]([N:16]1[CH2:20][CH2:19][CH2:18][C:17]1=[N:21][C:31]([NH:30][C:24]1[C:23]([CH3:22])=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:29])=[O:32])[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 3

HCID 7533CyclamateHCID 987872,6-Xylyl isocyanateHCID 124490221-n-Butyl-2-iminopyrrolidine

Product 1

HCID 537610961-(1-n-Butyl-2-pyrrolidylidene)-3-(2,6-dimethylphenyl)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 7.36 g. (0.05 mole) of 2,6-dimethylphenylisocyanate is added. The reaction mixture is stirred at room temperature for 31/2 hours and then evaporated to dryness in vacuo leaving an oily residue which crystallizes on cooling. Recrystallization from ethylacetate yields the pure product, 1-(1-n-butyl-2-pyrrolidylidene)-3-(2,6-dimethylphenyl)urea, m.p.=93°-95° C.

Workup

  1. dry with materialAfter drying over K2CO3
  2. filtrationthe benzene solution is filtered through diatomaceous earth and 7.36 g
  3. customevaporated to dryness in vacuo
  4. customleaving an oily residue which
  5. customcrystallizes
  6. temperatureon cooling
  7. customRecrystallization from ethylacetate

Sources & evidence

ORD record
ord-24b5a99c451a48b7a801051a129eee4e
Source dataset
uspto-grants-1977_09
Patent number
US04046909

Reaction notes

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