Ammonia → HCID 21504226, compound

HRID 1288237Notes

Reaction equation

HRID 1288237 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.Cl.[NH3:12].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19]([O-:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1.[Na+]>C(O)C.O>[C:13]1([CH3:23])[CH:14]=[CH:15][C:16]([S:19]([OH:22])(=[O:20])=[O:21])=[CH:17][CH:18]=1.[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH2:12])=[NH:10])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 222Ammonia2×HCID 313Hydrochloric AcidHCID 68016Benzeneacetonitrile, 4-fluoro-HCID 3720192Sodium 4-methylbenzenesulfonate

Product 1

HCID 21504226HCID 21504226, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 4-fluorophenylacetonitrile (71 g.) and dry ethanol (27.6 g.) was cooled in an ice-bath and dry hydrogen chloride was passed in until a weight increase of 25.5 g. was obtained. The mixture was allowed to stand at room temperature for 3 days and then treated portionwise, with vigorous shaking and occasional cooling, with a saturated solution of ammonia in dry ethanol. Addition was continued until a smell of ammonia persisted. The mixture was allowed to stand at room temperature for 2 days and then filtered. The filtrate was treated with a saturated aqueous solution of 1.1 equivalents of sodium p-toluenesulphonate and diluted with water. The crystalline precipitate was removed and recrystallised from ethanol to give pure 4-fluorophenylacetamidine p-toluenesulphonate, m.p. 215°-218°. The following amidines were also prepared by Method E; crystallisation solvents are given in brackets:

Workup

  1. temperaturewas cooled in an ice-bath
  2. temperatureincrease of 25.5 g
  3. customwas obtained
  4. additiontreated portionwise
  5. additionAddition
  6. waitto stand at room temperature for 2 days
  7. filtrationfiltered
  8. customThe crystalline precipitate was removed
  9. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-4b06163f952a4195b805ac31f3e7bd25
Source dataset
uspto-grants-1976_10
Patent number
US03987158

Reaction notes

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