Acetone → 3'-[1-Hydroxy-2-(2-imino-3-thiazolidinyl)ethyl]acetanilide hydrochloride

HRID 597571Notes

Reaction equation

HRID 597571 reaction equation
Br.[NH:2]=[C:3]1[N:7]([CH2:8][C:9]([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[NH:14][C:15](=[O:17])[CH3:16])=[O:10])[CH2:6][CH2:5][S:4]1.[BH4-].[Na+].[ClH:23].CC(C)=O>C(O)C>[ClH:23].[OH:10][CH:9]([C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=1)[NH:14][C:15](=[O:17])[CH3:16])[CH2:8][N:7]1[CH2:6][CH2:5][S:4][C:3]1=[NH:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric Acid2×HCID 4311764Sodium borohydride2×HCID 214456433'-[(2-Imino-3-thiazolidinyl)acetyl]acetanilide hydrobromide

Product 1

HCID 214456393'-[1-Hydroxy-2-(2-imino-3-thiazolidinyl)ethyl]acetanilide hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred slurry of 63.47 g. (0.177 mole) of 3'-[(2-imino-3-thiazolidinyl)acetyl]acetanilide hydrobromide (Example 3) in 1 liter of 95% ethanol, maintained at 5° C., is added 5.70 g. (0.15 mole) of sodium borohydride. After stirring 40 minutes an additional 4.10 g. of sodium borohydride is added and the mixture is acidified with hydrochloric acid and evaporated under reduced pressure. The residue is partitioned between chloroform and dilute aqueous ammonium hydroxide. Two further chloroform extracts are combined with the original, washed with brine, dried (sodium sulfate) and evaporated to give an oil. Treatment with acetone gives 26.77 g. (48%) of white crystalline hydrochloride, which has melting point 235°-237° C. Anal: Calcd. for C13H18CIN3O2S:x Calcd: C, 49.44; H, 5.74; Cl, 11.23; N, 13.31; S, 10.15. Found: C, 49.87; H, 5.27; Cl, 11.51; N, 13.25; S, 10.40.

Workup

  1. additionis added 5.70 g
  2. customevaporated under reduced pressure
  3. customThe residue is partitioned between chloroform and dilute aqueous ammonium hydroxide
  4. washwashed with brine
  5. dry with materialdried (sodium sulfate)
  6. customevaporated
  7. customto give an oil

Sources & evidence

ORD record
ord-ee1366908ec8465794766898a70f1d90
Source dataset
uspto-grants-1977_03
Patent number
US04014892

Reaction notes

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