Water → HCID 12888773, compound

HRID 1995275Notes

Reaction equation

HRID 1995275 reaction equation
[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[CH:5][N:4]([CH3:9])[N:3]=1.[H-].[Na+].Cl[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[N+:20]([O-:22])=[O:21].O>O1CCCC1>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([NH:1][C:2]2[C:6]([C:7]#[N:8])=[CH:5][N:4]([CH3:9])[N:3]=2)=[C:14]([N+:20]([O-:22])=[O:21])[CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 69772,5-DichloronitrobenzeneHCID 24758Sodium hydrideHCID 106542131-Methyl-3-amino-4-cyanopyrazole

Product 1

HCID 12888773HCID 12888773, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Amino-1-methylpyrazole-4-carbonitrile (Helv. Chim. Acta (1959) 42 763) (3.66 g) was stirred in dry tetrahydrofuran (40 ml). Sodium hydride (50% oil dispersion, 2.28 g) was added and the mixture was stirred for 10 minutes. 2,5-Dichloronitrobenzene (5.76 g) was added and the solution stirred under nitrogen for 20 hours. Water was added dropwise to destroy any excess sodium hydride, then the solution was poured on to a mixture of ice and dilute hydrochloric acid. After standing for 1 hour the brick-red precipitate was filtered, washed with water and dried. Crystallisation from ethanol-ethyl acetate afforded the product m.p. 205° C.

Workup

  1. stirringthe solution stirred under nitrogen for 20 hours
  2. customto destroy any excess sodium hydride
  3. additionthe solution was poured on to a mixture of ice and dilute hydrochloric acid
  4. waitAfter standing for 1 hour
  5. filtrationthe brick-red precipitate was filtered
  6. washwashed with water
  7. customdried
  8. customCrystallisation from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-8616279523904d728be7509e0859123b
Source dataset
uspto-grants-1983_09
Patent number
US04404137

Reaction notes

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