4-Methoxythiophene-3-carbohydrazide → 4-Methoxy-3-thiophenecarbonyl azide

HRID 2107620Notes

Reaction equation

HRID 2107620 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:8]([NH:10][NH2:11])=[O:9])=[CH:5][S:6][CH:7]=1.[N:12]([O-])=O.[Na+]>Cl.C(O)(=O)C.C(Cl)(Cl)Cl.O>[CH3:1][O:2][C:3]1[C:4]([C:8]([N:10]=[N+:11]=[N-:12])=[O:9])=[CH:5][S:6][CH:7]=1

Participants

7

Reactant 2

HCID 27367824-Methoxythiophene-3-carbohydrazideHCID 23668193Sodium Nitrite

Product 1

HCID 230461504-Methoxy-3-thiophenecarbonyl azide

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

4-Methoxy-3-thiophenecarboxylic acid hydrazide (20 g, 0.116 mol) in 3N hydrochloric acid (200 ml), acetic acid (200 ml) and chloroform (300 ml) was cooled to 0°. Sodium nitrite (8 g, 0.116 mol) in water (25 ml) was added dropwise whilst maintaining the temperature at 0°. On completion of the addition the reaction mixture was allowed to warm up to room temperature. The organic layer was separated, washed with sodium bicarbonate solution (3 times), dried over sodium sulphate and the solvent evaporated without heat to give the title compound as a buff-coloured solid, 21.2 g.

Workup

  1. temperaturewhilst maintaining the temperature at 0°
  2. additionOn completion of the addition the reaction mixture
  3. customThe organic layer was separated
  4. washwashed with sodium bicarbonate solution (3 times)
  5. dry with materialdried over sodium sulphate
  6. customthe solvent evaporated
  7. temperaturewithout heat

Sources & evidence

ORD record
ord-cb08a73f1c2448f9a9ae105d013b4371
Source dataset
uspto-grants-1990_06
Patent number
US04935431

Reaction notes

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