Ammonia → 6487-98-5

HRID 1288238Notes

Reaction equation

HRID 1288238 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH2:10][C:11]#[N:12])[CH:7]=[CH:8][CH:9]=1.[NH3:13]>C(O)C>[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH2:10][C:11]([NH2:13])=[NH:12])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 313Hydrochloric AcidHCID 88310(3-Methoxyphenyl)acetonitrile

Product 1

HCID 189389456487-98-5

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Dry hydrogen chloride was passed into a mixture of 3-methoxyphenylacetonitrile (19.7 g.) and dry ethanol (6.8 g., 7.8 ml.) until a weight increase of 5 g. was obtained. The mixture was allowed to stand at room temperature for 3 days and the solid mass was broken up and 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 warmed and filtered to remove a small amount of ammonium chloride. The filtrate was diluted with ether and the crystalline precipitate was removed and recrystallised from a mixture of ethanol and ether to give pure 3-methoxy-phenylacetamidine hydrochloride, m.p. 142°-144°.

Workup

  1. temperatureincrease of 5 g
  2. customwas obtained
  3. additiontreated portionwise
  4. additionAddition
  5. waitto stand at room temperature for 2 days
  6. temperaturewarmed
  7. filtrationfiltered
  8. customto remove a small amount of ammonium chloride
  9. additionThe filtrate was diluted with ether
  10. customthe crystalline precipitate was removed
  11. customrecrystallised from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-5ca35bffaefa49f499dbfc593db3b48b
Source dataset
uspto-grants-1976_10
Patent number
US03987158

Reaction notes

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