Hydrochloric Acid → 4-(Benzyloxy)butanimidamide--hydrogen chloride (1/1)

HRID 544566Notes

Reaction equation

HRID 544566 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]#[N:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCO.[ClH:17].[NH4+:18].[Cl-]>C(Cl)Cl.CO>[ClH:17].[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([NH2:18])=[NH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 25517Ammonium ChlorideHCID 2045821385174-51-2

Product 1

HCID 204582074-(Benzyloxy)butanimidamide--hydrogen chloride (1/1)

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-benzyloxybutyronitrile (16.5 g.) and EtOH (8.6 g.) in CH2Cl2 (100 ml.) was saturated with HCl gas at 0° and the mixture kept at 0° for 6 days. The resulting suspension was evaporated to dryness in vacuo and the residue was slurried with dry ether. The insoluble solid was added to 40% aqueous K2CO3 (120 g.) at 0° and the oil which separated was extracted with CH2Cl2 (2×100 ml.). The CH2Cl2 layer was washed with a little water, brine and then dried to give the crude imidate (14 g.). This was stirred with NH4Cl (3.5 g.) in MeOH (100 ml.) for 24 hours and the solution was evaporated to give a crude sample (14.6 g.) of 4-benzyloxybutanamidine hydrochloride.

Workup

  1. customThe resulting suspension was evaporated to dryness in vacuo
  2. additionThe insoluble solid was added to 40% aqueous K2CO3 (120 g.) at 0°
  3. customthe oil which separated
  4. extractionwas extracted with CH2Cl2 (2×100 ml.)
  5. washThe CH2Cl2 layer was washed with a little water, brine
  6. customdried
  7. customto give the crude imidate (14 g.)
  8. customthe solution was evaporated

Sources & evidence

ORD record
ord-425769538c9c41858351b939d69b0122
Source dataset
uspto-grants-1984_05
Patent number
US04451463

Reaction notes

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