Ethanol → HCID 20334096, compound

HRID 1706685Notes

Reaction equation

HRID 1706685 reaction equation
Br[CH:2]([C:9](=O)[CH2:10][CH2:11][C:12]([O-:14])=[O:13])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:16]([NH2:19])(=[S:18])[CH3:17].[CH2:20](O)[CH3:21]>>[CH3:17][C:16]1[S:18][C:10]([CH2:11][C:12]([O:14][CH2:20][CH3:21])=[O:13])=[C:9]([CH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:19]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 2723949ThioacetamideHCID 20334089HCID 20334089, compound

Product 1

HCID 20334096HCID 20334096, compoundYield 54%

Procedure

The crude product obtained in step (a) is dissolved in anhydrous ethanol (150 ml) with thioacetamide (37.5 g; 0.5 mole). The mixture is stirred for 70 hours at room temperature, after which the ethanol is distilled off and the residue is taken up into water and ethyl ether. The ether phase is repeatedly extracted with 2 N sulfuric acid, and is then combined with the aqueous phase. The latter is adjusted to pH 7: the oil which separates is extracted with ether and distilled under reduced pressure: b.p.0.2 =135°-140° C.; Weight: 78.5 g. Overall yield: 54%.

Workup

  1. distillationafter which the ethanol is distilled off
  2. extractionThe ether phase is repeatedly extracted with 2 N sulfuric acid
  3. extractionthe oil which separates is extracted with ether
  4. distillationdistilled under reduced pressure
  5. customb.p.0.2 =135°-140° C.

Sources & evidence

ORD record
ord-a616ceae2ace483fa6d3592afbe3f566
Source dataset
uspto-grants-1980_06
Patent number
US04208420

Reaction notes

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