Ammonia → 2-Propyloxybenzamidine Hydrochloride

HRID 437418Notes

Reaction equation

HRID 437418 reaction equation
C(O)C.[ClH:4].[CH2:5]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([NH2:13])=[NH:12])[CH2:6][CH3:7].N.F[B-](F)(F)F.C(OC1C=CC=CC=1C(=N)OCC)CC>C(O)C>[ClH:4].[CH2:5]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([NH2:13])=[NH:12])[CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 681171842-n-Propoxybenzamidine hydrochloride EthanolHCID 86734866Ethyl 2-n-propoxybenzimidate fluoroborate

Product 1

HCID 122542252-Propyloxybenzamidine HydrochlorideYield 76.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-n-Propoxybenzamidine hydrochloride Ethanol (100 ml.) containing 6.5 g. of ammonia was added during five minutes to a stirred suspension of ethyl 2-n-propoxybenzimidate fluoroborate (44.0 g.) in ethanol (25 ml.). The resulting solution was stirred at 25° for 20 hours. The solution was reduced to dryness and the residue partitioned between diethyl ether and 5N sodium hydroxide. The ether layer was washed with brine, dried over sodium sulfate, and concentrated. A solution of the residue in ether (500 ml.) and ethanol (50 ml.) was treated with hydrogen chloride to precipitate 2-n-propoxybenzamidine hydrochloride (28.8 g., 76.6% yield), m.p. 184°-186.5°.

Workup

  1. customthe residue partitioned between diethyl ether and 5N sodium hydroxide
  2. washThe ether layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. additionA solution of the residue in ether (500 ml.) and ethanol (50 ml.) was treated with hydrogen chloride

Sources & evidence

ORD record
ord-fa2cda12d7b54effa2b95dbcbb3676b3
Source dataset
uspto-grants-1977_06
Patent number
US04031093

Reaction notes

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