Ammonia → HCID 12115520, compound

HRID 1765470Notes

Reaction equation

HRID 1765470 reaction equation
CO[CH:3](OC)[C:4](=[N:7][OH:8])[C:5]#[N:6].Cl.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][NH2:20])=[CH:15][CH:14]=1.Cl.N>CO.O>[NH2:6][C:5]1[N:19]([C:16]2[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=2)[N:20]=[CH:3][C:4]=1[N:7]=[O:8]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 713615623,3-Dimethoxy-2-hydroxyiminopropionitrile

Product 1

HCID 12115520HCID 12115520, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
5 °C

Procedure

To a flask having an inner volume of 25 ml and equipped with a stirring device, a thermometer and a reflux condenser were charged 2.97 g (20 mmol) of 3,3-dimethoxy-2-hydroxyiminopropionitrile with a purity of 96.9% by weight synthesized in the same manner as in Example 1, 3.96 g (21 mmol) of 4-chlorophenylhydrazine hydrochloride with a purity of 95% by weight, 1.4 ml of water, 10 ml of methanol and 1.3 ml (15 mmol) of conc. hydrochloric acid, and the mixture was reacted at 50 to 52° C. for 2 hours. After completion of the reaction, 25 ml of water and 5 ml of methanol were added to the mixture to cool the same up to 10° C., and 2.3 ml (37.9 mmol) of 28% by weight aqueous ammonia was gradually added dropwise to the mixture and the resulting mixture was stirred for 30 minutes while maintaining the liquid temperature to 5° C. or lower. Precipitated crystals were collected by filtration, and then, the crystals were washed with 10 ml of cold water and dried under reduced pressure to obtain 3.73 g of 5-amino-1-(4-chlorophenyl)-4-nitrosopyrazole (Isolation yield: 74.3%) as a yellowish solid with a purity of 88.7% by weight (absolute calibration curve method by high performance liquid chromatography).

Workup

  1. customTo a flask having
  2. customan inner volume of 25 ml and equipped with a stirring device
  3. customthe mixture was reacted at 50 to 52° C. for 2 hours
  4. additionwere added to the mixture
  5. additionwas gradually added dropwise to the mixture
  6. customPrecipitated crystals
  7. filtrationwere collected by filtration
  8. washthe crystals were washed with 10 ml of cold water
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-e30cc665e8ad49d0b946cc499fac9c08
Source dataset
uspto-grants-2007_06
Patent number
US07227032B2

Reaction notes

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