Acetic Acid → HCID 19956208, compound

HRID 1779490Notes

Reaction equation

HRID 1779490 reaction equation
Br.[O:2]([CH2:4][CH2:5][Br:6])[NH2:3].C(O)(=O)C.N1C=CC=CC=1.[CH3:17][CH:18]1[C:25]2[N:24]3[CH:26]=[CH:27][CH:28]=[C:23]3[CH2:22][C:21]=2[S:20][C:19]1=O>C(O)C>[CH3:17][C:18]1[C:25]2[N:24]3[CH:26]=[CH:27][CH:28]=[C:23]3/[C:22](=[N:3]/[O:2][CH2:4][CH2:5][Br:6])/[C:21]=2[S:20][CH:19]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1049PyridineHCID 19077315O-(2-bromoethyl)hydroxylamine hydrobromideHCID 19956227HCID 19956227, compound

Product 1

HCID 19956208HCID 19956208, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add 5 g of 2-aminoxy-1-bromoethane hydrobromide, 1.5 mol of glacial acetic acid and 1.6 ml of pyridine in succession to a suspension of 1.43 g of 3-methyl-8H-thieno[2,3-d]pyrrolo[1,2-a]pyrrol-2-one (Preparation 29) in 70 ml of ethanol. The reaction mixture is heated at reflux for 3 hours, then the ethanol is removed under reduced pressure and the residue is extracted with 100 ml of diethyl ether. After washing with water, drying, concentrating to dryness and working up again in a diethyl ether/petroleum ether mixture, 1:1, the title compound is obtained in the form of a powder.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 3 hours
  3. customthe ethanol is removed under reduced pressure
  4. extractionthe residue is extracted with 100 ml of diethyl ether
  5. washAfter washing with water
  6. customdrying
  7. concentrationconcentrating to dryness

Sources & evidence

ORD record
ord-e7537ae1bf8a495f8f147288b39e0813
Source dataset
uspto-grants-1997_05
Patent number
US05627203

Reaction notes

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