Water → HCID 12888773, compound

HRID 1719678Notes

Reaction equation

HRID 1719678 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. Crystallization 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. customCrystallization from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-a8943e9619eb4dac9a83c23df93db7d8
Source dataset
uspto-grants-1985_09
Patent number
US04542131

Reaction notes

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