Guanidine Hydrochloride → N-carbamimidoylbenzamide

HRID 433341Notes

Reaction equation

HRID 433341 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].C[O-].[Na+].[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CO>[C:3]([NH:5][C:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[NH:2])[NH2:4]

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 7412Benzoyl chlorideHCID 10942334Sodium Methoxide

Product 1

HCID 178513056N-carbamimidoylbenzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A four neck flask (3 liters) equipped with a thermometer and a stirrer was charged with 573.2 g (6.0 mole) of guanidine hydrochloride and 1.5 liter of methanol and cooled to 20° C. Slowly dropwise added thereto was 324.1 g (6.0 mole) of sodium methoxide crystal at 20° C. or lower and stirred for 3 hours. Deposited crystals were filtered off. The mother liquor was charged to the four neck flask (3 liters) equipped with the above devices, and 337.4 g (2.4 mole) of benzoyl chloride was slowly dropwise added at 15° C. or lower and stirred for 12 hours. Deposited crystals were filtered off, and the mother liquor was concentrated under reduced pressure to obtain white crystals. The resulting crystals were sufficiently washed with 3 liters of deionized water and dried under reduced pressure, whereby the intended compound (white crystals) was obtained.

Workup

  1. customA four neck flask (3 liters) equipped with a thermometer and a stirrer
  2. additionSlowly dropwise added
  3. customat 20° C.
  4. filtrationDeposited crystals were filtered off
  5. additionThe mother liquor was charged to the four neck flask (3 liters)
  6. additionwas slowly dropwise added at 15° C.
  7. stirringlower and stirred for 12 hours
  8. filtrationDeposited crystals were filtered off
  9. concentrationthe mother liquor was concentrated under reduced pressure
  10. customto obtain white crystals
  11. washThe resulting crystals were sufficiently washed with 3 liters of deionized water
  12. customdried under reduced pressure, whereby the intended compound (white crystals)
  13. customwas obtained

Sources & evidence

ORD record
ord-abb53206dc4b4900bc7cccddeda03449
Source dataset
uspto-grants-2003_12
Patent number
US06667356B2

Reaction notes

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