Guanidine → HCID 178513087, compound

HRID 2058648Notes

Reaction equation

HRID 2058648 reaction equation
[NH2:1][C:2]([NH2:4])=[NH:3].[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[CH:13]([Br:17])[C:14](Br)=[O:15].[OH-].[Na+]>O.CC(C)=O>[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[CH:13]([Br:17])[C:14]([NH:3][C:2]([NH2:4])=[NH:1])=[O:15]

Participants

6

Reactant 3

HCID 3520GuanidineHCID 14798Sodium HydroxideHCID 20549424HCID 20549424, compound

Product 1

HCID 178513087HCID 178513087, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a solution of 0.072 mols guanidine (from 6.9 g guanidine hydrochloride and 3 g NaOH) in 100 ml water, 20 g (0.06 mols) 2-(2,6-dichlorophenyl)-2-bromo-acetyl-bromide in 50 ml acetone and 2.4 g (0.06 mols) NaOH in 50 ml water at 10 degrees C. are simultaneously added dropwise. After one hour, the organic phase is extracted with methylene chloride, filtered, and further extracted in a counter-current manner with 1 N hydrochloric acid. The acid phase is then adjusted to an alkaline pH and extracted with CH2Cl2. Subsequent to the evaporation of the methylene chloride, the guanidine base is obtained. It has decomposition point of 155 degrees C. The hydrochloride is prepared in the usual way using ethanolic hydrochloric acid, and is recrystalized from a mixture of acetic acid and ethanol. The decomposition point is 228-229 degrees C.

Workup

  1. customat 10 degrees C
  2. additionare simultaneously added dropwise
  3. extractionthe organic phase is extracted with methylene chloride
  4. filtrationfiltered
  5. extractionfurther extracted in a counter-current manner with 1 N hydrochloric acid
  6. extractionextracted with CH2Cl2
  7. customSubsequent to the evaporation of the methylene chloride

Sources & evidence

ORD record
ord-4647065717584dcaa1aff50bf8282b29
Source dataset
uspto-grants-1982_03
Patent number
US04318915

Reaction notes

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