Triethylamine → (3-Chloropropanoyl)urea

HRID 345170Notes

Reaction equation

HRID 345170 reaction equation
C1C[NH:6][C:4](=[O:5])[NH:3]C1.C(N(CC)CC)C.[Cl:15][CH2:16][CH2:17][C:18](Cl)=[O:19]>C1(C)C=CC=CC=1>[Cl:15][CH2:16][CH2:17][C:18]([NH:3][C:4]([NH2:6])=[O:5])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 693643-Chloropropionyl chlorideHCID 746152(1H)-Pyrimidinone, tetrahydro-

Product 1

HCID 12937417(3-Chloropropanoyl)ureaYield 79.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
5 °C

Procedure

20.0 g of N,N'-trimethyleneurea are partially dissolved in 1000 ml of toluene under reflux and admixed with 20.2 g of triethylamine and then dropwise, in the course of 90 minutes, with a solution of 25.4 g of 3-chloropropionyl chloride. Subsequent stirring for 30 minutes, cooling down to 5° C., removal of undissolved matter by filtration and evaporating the filtrate in vacuo gives 24 g of chloropropionylurea of the formula ##STR70## as a beige powder.

Workup

  1. temperatureunder reflux
  2. customin the course of 90 minutes
  3. customremoval of undissolved matter
  4. filtrationby filtration
  5. customevaporating the filtrate in vacuo

Sources & evidence

ORD record
ord-e25446250eeb40bdb22986ef2666127e
Source dataset
uspto-grants-1991_10
Patent number
US05055567

Reaction notes

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