2-Chloroethyl isocyanate → 1-(2-Chloroethyl)-3-(dicyclopropylmethyl)urea

HRID 867078Notes

Reaction equation

HRID 867078 reaction equation
[CH:1]1([CH:4]([NH2:8])[CH:5]2[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.[Cl:9][CH2:10][CH2:11][N:12]=[C:13]=[O:14]>O1CCCC1>[CH:1]1([CH:4]([CH:5]2[CH2:7][CH2:6]2)[NH:8][C:13]([NH:12][CH2:11][CH2:10][Cl:9])=[O:14])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 83390(Dicyclopropylmethyl)amine

Product 1

HCID 988261-(2-Chloroethyl)-3-(dicyclopropylmethyl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution made from 13.4 g of dicyclopropylmethylamine in 30 ml tetrahydrofuran is added dropwise to a solution of 13 g of β-chloroetyl isocyanate in 15 ml tetrahydrofuran while maintaining the inner temperature from 0° to +5° C. Then, the reaction mixture is kept at room temperature for 15 hours. Afterwards, the solution is evaporated to dryness and the dry residue, weighing 26.5 g, is used as such for the next step of the synthesis. For analytical purpose, a sample of the raw urea is recrystallised from acetonitrile. The N-(dicyclopropylmethyl) N-(β-chloroethyl) urea occurs as white crystals melting at 103°-104° C. with decomposition.

Workup

  1. temperaturewhile maintaining the inner temperature from 0° to +5° C
  2. customAfterwards, the solution is evaporated to dryness
  3. customsuch for the next step of the synthesis
  4. customFor analytical purpose, a sample of the raw urea is recrystallised from acetonitrile

Sources & evidence

ORD record
ord-7e362a03602c4508823701aeddbc55a1
Source dataset
uspto-grants-1978_07
Patent number
US04102890

Reaction notes

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