Water → Indapamide

HRID 1589422Notes

Reaction equation

HRID 1589422 reaction equation
[CH2:1]([N:4]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH:5][C:6](=O)[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([S:14](=[O:17])(=[O:16])[NH2:15])[CH:8]=1)[CH:2]=[CH2:3].[OH2:25]>Cl.Cl.[Cl-].[Cl-].[Zn+2].[Cl-].[Zn+2].[Cl-]>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]([NH:5][N:4]2[C:1]3[C:21](=[CH:22][CH:23]=[CH:3][CH:2]=3)[CH2:20][CH:19]2[CH3:24])=[O:25])=[CH:8][C:9]=1[S:14](=[O:16])(=[O:17])[NH2:15]

Participants

6

Reactant 2

HCID 962WaterHCID 155715021-Allyl-1-phenyl-2-(3-sulfamoyl-4-chlorobenzoyl)-hydrazine

Product 1

HCID 3702Indapamide

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 21263579ZINC chloride hydrogen chlorideCatalystHCID 313Hydrochloric AcidSolvent

Procedure

In a 50 ml round bottom was placed 8 grams of Lucas reagent. The reagent is prepared by dissolving 16 grams of anhydrous zinc chloride in 10 ml of concentrated hydrochloric acid. To this reagent was added 100 mg (0.27 mmols) of 1-allyl-1-phenyl-2-(3-sulfamoyl-4-chlorobenzoyl)-hydrazine with stirring under nitrogen for a short time to dissolve the solid. The reaction cyclized at 60° C. over 6 hours. The reactant was worked up by pouring the cooled reaction mixture into water and extracting the product into ethyl acetate. The ethyl acetate phase was cross washed several times with water and sodium bicarbonate solution. The ethyl acetate solution is dried with magnesium sulfate, clarified and evaporated to dryness yielding 84 mg of crude 1-(4-chloro-3-sulfamoylbenzamido)-2-methylindoline.

Workup

  1. customThe reagent is prepared
  2. dissolutionto dissolve the solid
  3. additionby pouring
  4. extractionextracting the product into ethyl acetate
  5. dry with materialThe ethyl acetate solution is dried with magnesium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-e8e0c6a26c7f43feac79a0a4b0e6e1cb
Source dataset
uspto-grants-1986_02
Patent number
US04570001

Reaction notes

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