Propargyl bromide → HCID 178459972, compound

HRID 1981087Notes

Reaction equation

HRID 1981087 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[N:11]=[C:12]1[NH:16][CH2:15][CH2:14][N:13]1[OH:17].[CH2:18](Br)[C:19]#[CH:20]>CN(C)C=O>[ClH:3].[Cl:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([Cl:3])[C:5]=1[N:11]=[C:12]1[NH:16][CH2:15][CH2:14][N:13]1[O:17][CH2:20][C:19]#[CH:18]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 178526276HCID 178526276, compound

Product 1

HCID 178459972HCID 178459972, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.31 g. of sodium hydride (55% strength suspension) are added to a solution of 6.15 g. of 2-[(2,6-dichlorophenyl)imino]-1-hydroxyimidazolidine in 45 ml. of absolute dimethylformamide at a temperature of 25°. After 30 minutes, 4.16 g. of propargyl bromide are added dropwise. After 30 minutes, the mixture is poured onto 500 ml. of a saturated solution of sodium chloride and the aqueous phase is extracted with ether. The ether extracts are washed with aqueous hydrochloric acid. The aqueous extracts are then rendered basic with 3N caustic soda solution and extracted with ether. After evaporating off the solvent, the residue is dissolved in ether, and hydrogen chloride in dioxane is added. The residue is recrystallized from methanol/acetonitrile, whereupon 2-[(2,6-dichlorophenyl)imino]-1-(2-propynyloxy)-imidazolidine hydrochloride, m.p. 198°-199° (from methanol/acetonitrile) is obtained.

Workup

  1. customat a temperature of 25°
  2. waitAfter 30 minutes
  3. additionthe mixture is poured onto 500 ml
  4. extractionof a saturated solution of sodium chloride and the aqueous phase is extracted with ether
  5. washThe ether extracts are washed with aqueous hydrochloric acid
  6. extractionextracted with ether
  7. customAfter evaporating off the solvent
  8. dissolutionthe residue is dissolved in ether
  9. additionhydrogen chloride in dioxane is added
  10. customThe residue is recrystallized from methanol/acetonitrile, whereupon 2-[(2,6-dichlorophenyl)imino]-1-(2-propynyloxy)-imidazolidine hydrochloride
  11. customm.p. 198°-199° (from methanol/acetonitrile) is obtained

Sources & evidence

ORD record
ord-8a71bb1107f640e6b8a25d568c6b67c5
Source dataset
uspto-grants-1985_04
Patent number
US04511720

Reaction notes

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