Sodium Bicarbonate → HCID 140332947, compound

HRID 326162Notes

Reaction equation

HRID 326162 reaction equation
Cl[CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:10][CH:9]=1)[C:3](OC)=[O:4].[NH2:23][C:24]([NH2:26])=[S:25].C(=O)([O-])O.[Na+]>S1(CCCC1)(=O)=O>[NH:23]=[C:24]1[NH:26][C:3](=[O:4])[CH:2]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:10][CH:9]=2)[S:25]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 12830902HCID 12830902, compound

Product 1

HCID 140332947HCID 140332947, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

A mixture of 10.0 g methyl 2-chloro-3-[4-(2-morpholinoethyloxy)phenyl]propionate and 4.64 g thiourea is heated in the presence of 100 ml of sulfolane at 120° C. for 4 hours. After cooling, a saturated aqueous solution of sodium hydrogen carbonate is added and the mixture is extracted with ethyl acetate. The extract is washed with water, dried over sodium sulfate and distilled to remove the ethyl acetate, whereupon 4.1 g (40.2%) of 2-imino-5-[4-(2-morpholinoethyloxy)benzyl]thiazolidin-4-one is obtained as crystals. These crystals are recrystallized from ethyl acetate-methanol. Colorless needles, m.p. 189°-190° C.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe extract is washed with water
  4. dry with materialdried over sodium sulfate
  5. distillationdistilled
  6. customto remove the ethyl acetate

Sources & evidence

ORD record
ord-68fcf9ed1882430c95a9c4c6b1115b43
Source dataset
uspto-grants-1984_04
Patent number
US04444779

Reaction notes

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