N-(2-Chloroethyl)-N'-(dicyclopropylmethyl)thiourea → 2-(Dicyclopropylmethylamino) thiazoline

HRID 867081Notes

Reaction equation

HRID 867081 reaction equation
[CH:1]1([CH:4]([NH:8][C:9]([NH:11][CH2:12][CH2:13]Cl)=[S:10])[CH:5]2[CH2:7][CH2:6]2)[CH2:3][CH2:2]1>O>[CH:1]1([CH:4]([NH:8][C:9]2[S:10][CH2:13][CH2:12][N:11]=2)[CH:5]2[CH2:7][CH2:6]2)[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 54444247N-(2-Chloroethyl)-N'-(dicyclopropylmethyl)thiourea

Product 1

HCID 544409782-(Dicyclopropylmethylamino) thiazoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The raw N-(1,1-dicyclopropylmethyl) N'-(βchloroethyl) thiourea obtained by step (a) is suspended in 100 ml of water and dissolved by warming. After complete solution, the aqueous phase is extracted with ether; the organic phase is discarded. The aqueous solution is made alkaline by adding an excess of 30% soda. An oily fraction separates which is then extracted with ether. The organic solution is washed with water, dried on sodium sulphate, filtered and evaporated to dryness. The cristallized residue is purified by dissolving it in the minimum amount of hot cyclohexane. By standing the solution in a cool place, 6 g of 2-(dicyclopropylmethylamino) thiazoline melting at 127°-128° C. (with decomposition) are recovered.

Workup

  1. dissolutiondissolved
  2. temperatureby warming
  3. extractionAfter complete solution, the aqueous phase is extracted with ether
  4. additionby adding an excess of 30% soda
  5. extractionAn oily fraction separates which is then extracted with ether
  6. washThe organic solution is washed with water
  7. customdried on sodium sulphate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe cristallized residue is purified
  11. dissolutionby dissolving it in the minimum amount of hot cyclohexane
  12. customare recovered

Sources & evidence

ORD record
ord-347a55c7ea8740c1b1d2bf6fd0762337
Source dataset
uspto-grants-1978_07
Patent number
US04102890

Reaction notes

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