Water → Indapamide

HRID 1589421Notes

Reaction equation

HRID 1589421 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].FC(F)(F)S(O)(=O)=O.[OH2:33]>>[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:33])=[CH:8][C:9]=1[S:14](=[O:16])(=[O:17])[NH2:15]

Participants

4

Reactant 3

HCID 962WaterHCID 62406Trifluoromethanesulfonic acidHCID 155715021-Allyl-1-phenyl-2-(3-sulfamoyl-4-chlorobenzoyl)-hydrazine

Product 1

HCID 3702Indapamide

Procedure

In a 50 ml reaction vessel was placed 1 gram (2.73 mmols) of 1-allyl-1-phenyl-2-(3-sulfamoyl-4-chlorobenzoyl)-hydrazine and 10 ml of trifluoromethane sulfonic acid. The reaction mixture was stirred under a nitrogen atmosphere at ambient temperatures. After 15 minutes the solid dissolved and the reaction was allowed to proceed for a total of 4.75 hours. The reaction mixture was worked up by pouring the acid solution into 250 ml of water, extracting the precipitate into ethyl acetate, washing the ethyl acetate several times with water and sodium bicarbonate solution. The ethyl acetate phase was separated and dried with magnesium sulfate and clarified. The isolated product was further purified by dry column chromatography and then crystallized from 50% w/w methanol-acetone.

Workup

  1. customIn a 50 ml reaction vessel
  2. dissolutionAfter 15 minutes the solid dissolved
  3. customto proceed for a total of 4.75 hours
  4. extractionextracting the precipitate into ethyl acetate
  5. washwashing the ethyl acetate several times with water and sodium bicarbonate solution
  6. customThe ethyl acetate phase was separated
  7. dry with materialdried with magnesium sulfate
  8. customThe isolated product was further purified
  9. customby dry column chromatography
  10. customcrystallized from 50% w/w methanol-acetone

Sources & evidence

ORD record
ord-0028e305776c48deb22c5679b999c62c
Source dataset
uspto-grants-1986_02
Patent number
US04570001

Reaction notes

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