Triethylamine → 1-(3-Chloropropyl)-3-(4-cyanophenyl)urea

HRID 543188Notes

Reaction equation

HRID 543188 reaction equation
C(N(CC)CC)C.Cl.[Cl:9][CH2:10][CH2:11][CH2:12][NH2:13].[C:14]([C:16]1[CH:21]=[CH:20][C:19]([N:22]=[C:23]=[O:24])=[CH:18][CH:17]=1)#[N:15]>C(Cl)Cl>[Cl:9][CH2:10][CH2:11][CH2:12][NH:13][C:23]([NH:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]#[N:15])=[CH:17][CH:18]=1)=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1703804-Cyanophenyl isocyanateHCID 114690951-Propanamine, 3-chloro-, hydrochloride

Product 1

HCID 136067331-(3-Chloropropyl)-3-(4-cyanophenyl)ureaYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (13.8 g; 137 mmole) was slowly added to a mixture of 3-chloropropylamine hydrochloride (17.8 g; 137 mmole), 4-cyanophenyl isocyanate (19.7 g; 137 mmole), and methylene chloride (200 ml). The resulting solution was stirred until the mild exothermic reaction had subsided and the solvent was removed in vacuo. The product was dissolved in ether, washed with water, dried, and part of the ether removed. The colorless crystals which precipitated out were filtered and dried to give 1-(3-chloropropyl)-3-(4-cyanophenyl)urea (17.5 g; 54% yield). A small portion of the product was recrystallized from water/acetone to give pure product, m.p. 95°-97° C.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe product was dissolved in ether
  3. washwashed with water
  4. customdried
  5. custompart of the ether removed
  6. customThe colorless crystals which precipitated out
  7. filtrationwere filtered
  8. customdried

Sources & evidence

ORD record
ord-947cc628757a4abf9caf01116dc8f47a
Source dataset
uspto-grants-1987_04
Patent number
US04661481

Reaction notes

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