Methanol → HCID 13022915, compound

HRID 1106287Notes

Reaction equation

HRID 1106287 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([CH2:12][C:13](=O)[CH:14]=[CH:15]C(O)=O)[CH:8]=[CH:9][C:10]=1[Cl:11])(=[O:4])=[O:3].[OH-:20].[K+].[NH2:22][NH2:23].C[OH:25]>>[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([C:12]2[CH2:13][CH:14]([C:15]([OH:25])=[O:20])[NH:23][N:22]=2)[CH:8]=[CH:9][C:10]=1[Cl:11])(=[O:3])=[O:4]

Participants

5

Reactant 4

HCID 887MethanolHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 54447163HCID 54447163, compound

Product 1

HCID 13022915HCID 13022915, compound

Procedure

A mixture of 5.8 g of 5-[3(aminosulfonyl)-4-chlorophenyl]-4-oxo-2-pentenoic acid and 1.2 g of KOH in 50 ml of methanol is treated with 0.7 ml of hydrazine and the mixture is refluxed for 3 hours. Approximately 40 ml of methanol is removed in vacuo and 20 ml of water is added. The mixture is acidified to pH 6.5 with concentrated HCl and the resulting solid is filtered off and washed with ether to give 2.2 g of the title compound, melting point 125° C. dec.

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. customApproximately 40 ml of methanol is removed in vacuo and 20 ml of water
  3. additionis added
  4. filtrationthe resulting solid is filtered off
  5. washwashed with ether

Sources & evidence

ORD record
ord-b916547995734b8f9d0a135181c41550
Source dataset
uspto-grants-1982_01
Patent number
US04312990

Reaction notes

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