Hydrochloric Acid → 1-[3-[[1-[3-(Aminosulfonyl)-4-chlorophenyl]2,3-dihydro-3-oxo-1H-isoindol-1yl]thio]-2-methyl-1-oxopropyl]-L-proline

HRID 1106218Notes

Reaction equation

HRID 1106218 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[C:10](O)([C:11]3[CH:12]=[CH:13][C:14]([Cl:21])=[C:15]([S:17]([NH2:20])(=[O:19])=[O:18])[CH:16]=3)[NH:9][C:7](=[O:8])[C:5]=2[CH:6]=1.[SH:23][CH2:24][CH:25]([CH3:36])[C:26]([N:28]1[CH2:35][CH2:34][CH2:33][C@H:29]1[C:30]([OH:32])=[O:31])=[O:27].Cl>C(OCC)(=O)C>[NH2:20][S:17]([C:15]1[CH:16]=[C:11]([C:10]2([S:23][CH2:24][CH:25]([CH3:36])[C:26]([N:28]3[CH2:35][CH2:34][CH2:33][C@H:29]3[C:30]([OH:32])=[O:31])=[O:27])[C:4]3[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=3)[C:7](=[O:8])[NH:9]2)[CH:12]=[CH:13][C:14]=1[Cl:21])(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2732ChlorthalidoneHCID 128775471-(2-Methyl-3-sulfanylpropanoyl)-L-proline

Product 1

HCID 130226931-[3-[[1-[3-(Aminosulfonyl)-4-chlorophenyl]2,3-dihydro-3-oxo-1H-isoindol-1yl]thio]-2-methyl-1-oxopropyl]-L-prolineYield 48.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.69 g chlorthalidone, 2.5 g of 1-(3-mercapto-2-methyl-1-oxopropyl)-L-proline and 150 ml ethyl acetate is cooled by an ice bath and then saturated with HCl gas. This mixture is refluxed for one hour. The solvent is evaporated, the residue dissolved in warm saturated sodium bicarbonate solution, and the mixture extracted with ethyl acetate. The aqueous phase is separated and acidified at ice bath temperature. The resulting solid is filtered off, washed with water and dried to yield 1.3 g of the title compound.

Workup

  1. temperatureis cooled by an ice bath
  2. temperatureThis mixture is refluxed for one hour
  3. customThe solvent is evaporated
  4. dissolutionthe residue dissolved in warm saturated sodium bicarbonate solution
  5. extractionthe mixture extracted with ethyl acetate
  6. customThe aqueous phase is separated
  7. customacidified at ice bath
  8. filtrationThe resulting solid is filtered off
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-3487d77bc92d42d49d7493b3acae8727
Source dataset
uspto-grants-1982_01
Patent number
US04312809

Reaction notes

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