Ammonia → HCID 22251304, compound

HRID 1768333Notes

Reaction equation

HRID 1768333 reaction equation
N.Cl.[NH2:3][NH:4][C:5]([NH2:7])=[O:6].[C:8]1(C)[C:9]([S:14]([OH:17])(=[O:16])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=1>CO>[S:14]([C:9]1[CH:8]=[CH:13][C:12]([CH3:5])=[CH:11][CH:10]=1)([OH:17])(=[O:15])=[O:16].[NH2:3][NH:4][C:5]([NH2:7])=[O:6]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 69252-Methylbenzenesulfonic acidHCID 11236Semicarbazide hydrochloride

Product 1

HCID 22251304HCID 22251304, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At room temperature, NH3 (20 mL, 135 mmol, 7N in methanol) was added subsurface via syringe to a stirred slurry of semicarbazide hydrochloride (10.0 g, 90 mmol) in methanol (75 mL). After one hour, the solution was filtered to remove ammonium chloride. The filtrate was diluted with ethyl acetate (150 mL) and the resulting solution was concentrated to ˜300 mL by a reduced pressure distillation. The solution was filtered and treated with toluene sulfonic acid (17.1 g, 90 mmol). Upon acid addition, a white precipitate formed which was collected by filtration. The solid was rinsed with ethyl acetate (50 mL) and dried under reduced pressure.

Workup

  1. filtrationthe solution was filtered
  2. customto remove ammonium chloride
  3. additionThe filtrate was diluted with ethyl acetate (150 mL)
  4. concentrationthe resulting solution was concentrated to ˜300 mL by a reduced pressure distillation
  5. filtrationThe solution was filtered
  6. additionUpon acid addition
  7. customa white precipitate formed which
  8. filtrationwas collected by filtration
  9. washThe solid was rinsed with ethyl acetate (50 mL)
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-ca5fb03168934128b0f23e4951fec77c
Source dataset
uspto-grants-2007_06
Patent number
US07235671B2

Reaction notes

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