4-Bromophenyl isocyanate → 1-(4-Bromophenyl)-3-(1-pyrrolin-2-yl)urea

HRID 2399080Notes

Reaction equation

HRID 2399080 reaction equation
[Na].Cl.[NH2:3][C:4]1[CH2:8][CH2:7][CH2:6][N:5]=1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]=[C:17]=[O:18])=[CH:12][CH:11]=1>CC(C)=O>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([NH:3][C:4]2[CH2:8][CH2:7][CH2:6][N:5]=2)=[O:18])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 756094-Bromophenyl isocyanateHCID 5360545SodiumHCID 127789052-Amino-1-pyrroline hydrochloride

Product 1

HCID 214061831-(4-Bromophenyl)-3-(1-pyrrolin-2-yl)urea

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Following a procedure similar to that described in Example 2 but using 4.6 g. sodium in 300 ml. dry acetone, 23.2 g. 2-amino-1-pyrroline hydrochloride and 38.9 g. 4-bromophenyl isocyanate in 200 ml. dry acetone, there was obtained after recrystallization from ethyl alcohol 10.8 g. of the hydrochloride of 1-(4-bromophenyl)-3-(1-pyrrolin-2-yl)urea; m.p. 221°-224° C.

Workup

  1. customafter recrystallization from ethyl alcohol 10.8 g

Sources & evidence

ORD record
ord-46c563436fe24306b7e938638745ebba
Source dataset
uspto-grants-1977_05
Patent number
US04026938

Reaction notes

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