Hydrochloric Acid → HCID 178457009, compound

HRID 2390521Notes

Reaction equation

HRID 2390521 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].[C:5]1([N:11]=[C:12]=[S:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.N1C=CC=CC=1.Br[CH2:21][C:22](OC)=[O:23].Cl>CO>[C:5]1([N:11]2[C:22](=[O:23])[CH2:21][S:13]/[C:12]/2=[N:4]\[CH:1]([CH3:3])[CH3:2])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6363IsopropylamineHCID 7673Phenyl IsothiocyanateHCID 60984Methyl bromoacetate

Product 1

HCID 178457009HCID 178457009, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of isopropylamine (1.31 g, 22.19 mmol) in methanol (25 mL) is added portionwise phenylisothiocyanate (3.0 g, 22.19 mmol). The solution which becomes slightly warm during the addition is stirred at rt for 4 h before pyridine (2.63 g, 33.29 mmol) and methyl bromoacetate (3.39 g, 22.19 mmol) is added. The mixture is stirred for another 16 h at rt before it is poured onto 1 N aq. HCl (100 mL) and extracted with diethyl ether (150 mL). The aq. layer is neutralised by adding sat. aq. NaHCO3 and extracted with diethyl ether (4×150 mL). The organic extracts are dried over MgSO4 and evaporated. The remaining solid is suspended in diethyl ether/heptane, filtered off, washed with additional diethyl ether/heptane and dried to give 3-phenyl-2-[(Z)-isopropylimino]-thiazolidin-4-one.

Workup

  1. temperatureThe solution which becomes slightly warm during the addition
  2. additionis added
  3. extractionextracted with diethyl ether (150 mL)
  4. additionby adding sat. aq. NaHCO3
  5. extractionextracted with diethyl ether (4×150 mL)
  6. dry with materialThe organic extracts are dried over MgSO4
  7. customevaporated
  8. filtrationfiltered off
  9. washwashed with additional diethyl ether/heptane
  10. customdried

Sources & evidence

ORD record
ord-631bf44c402d44afa525cad9d605a3f1
Source dataset
uspto-grants-2012_09
Patent number
US08273779B2

Reaction notes

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