Sodium Azide → HCID 19778312, compound

HRID 2082399Notes

Reaction equation

HRID 2082399 reaction equation
Cl[C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([CH3:19])[C:3]=1[CH:20]=[O:21].[N-:22]=[N+]=[N-].[Na+]>CS(C)=O>[NH2:22][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([CH3:19])[C:3]=1[CH:20]=[O:21]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 11984127HCID 11984127, compound

Product 1

HCID 19778312HCID 19778312, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-Chloro-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methyl-1H-pyrazole-4-carboxaldehyde (1.2 g) and sodium azide (0.3 g) were heated at 70° under a nitrogen atmosphere in dimethyl sulphoxide (15 ml) for 8 hours. The solvent was removed in vacuo and the residue redissolved in methanol (20 ml) containing piperidine (1 ml). This mixture was cooled to 15° while hydrogen sulphide gas was bubbled in slowly for 3 hours. The mixture was worked up to give 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methyl-1H-pyrazole-4-carboxaldehyde, m.p. 169°-172°.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue redissolved in methanol (20 ml)
  3. additioncontaining piperidine (1 ml)
  4. temperatureThis mixture was cooled to 15° while hydrogen sulphide gas
  5. customwas bubbled in slowly for 3 hours

Sources & evidence

ORD record
ord-0600d24e9aa843c19919af9ccae0b4b4
Source dataset
uspto-grants-1993_02
Patent number
US05189053

Reaction notes

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