1-Butanol → HCID 12944222, compound

HRID 1577135Notes

Reaction equation

HRID 1577135 reaction equation
Cl[CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][N:17]([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])=[CH:10][CH:9]=1)[C:3]([O:5]C)=O.[NH2:24][C:25](N)=[S:26].C([OH:32])CCC>>[CH:18]([N:17]([CH2:16][CH2:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][CH:2]2[S:26][C:25](=[O:32])[NH:24][C:3]2=[O:5])=[CH:9][CH:10]=1)[CH:21]([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

4

Reactant 3

HCID 2631-ButanolHCID 2723790ThioureaHCID 12830901HCID 12830901, compound

Product 1

HCID 12944222HCID 12944222, compoundYield 65.2%

Conditions

Temperature
100 °C

Procedure

A mixture of 9.0 g methyl 2-chloro-3-{4-[2-(N,N-diisopropylamino)ethyloxy]phenyl}propionate and 2.4 g thiourea is heated in the presence of 100 ml of n-butanol at 100° C. for 15 hours. After cooling, the n-butanol is distilled off under reduced pressure, 100 ml of 2 N--HCl is added to the residue and the mixture is heated at 100° C. for 6 hours. After cooling, the reaction mixture is neutralized with a saturated aqueous solution of sodium hydrogen carbonate and extracted with ethyl acetate. The extract is washed with water, dried (over Na2SO4) and distilled to remove the ethyl acetate, whereupon 6.0 g (65.2%) of 5-{4-[2-(N,N-diisopropylamino)ethyloxy]benzyl}thiazolidine-2,4-dione is obtained as crystals. These crystals are recrystallized from ethanol. Colorless prisms, m.p. 134°-135° C.

Workup

  1. temperatureAfter cooling
  2. distillationthe n-butanol is distilled off under reduced pressure, 100 ml of 2 N
  3. additionHCl is added to the residue
  4. temperatureAfter cooling
  5. extractionextracted with ethyl acetate
  6. washThe extract is washed with water
  7. dry with materialdried (over Na2SO4)
  8. distillationdistilled
  9. customto remove the ethyl acetate

Sources & evidence

ORD record
ord-1df912dd22fe432baf59a24fca3bed04
Source dataset
uspto-grants-1981_09
Patent number
US04287200

Reaction notes

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