Acetic Anhydride → HCID 19092746, compound

HRID 487709Notes

Reaction equation

HRID 487709 reaction equation
[C:1]([NH:5][CH2:6][C:7]1[N:8]=[C:9]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:15]=3[CH:16]=2)[S:10][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[C:22](OC(=O)C)(=[O:24])[CH3:23]>C(OCC)(=O)C>[C:22]([N:5]([CH2:6][C:7]1[N:8]=[C:9]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:15]=3[CH:16]=2)[S:10][CH:11]=1)[C:1]([CH3:4])([CH3:2])[CH3:3])(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 19092812HCID 19092812, compound

Product 1

HCID 19092746HCID 19092746, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(tert-butylaminomethyl)-2-(5-hydroxybenzofuran-2-yl)thiazole (0.82 g) and acetic anhydride (0.75 g) in ethyl acetate (10 ml) was stirred under reflux for 4 hours. After being cooled, the resulting mixture was concentrated under reduced pressure. A solution of the resulting mixture in methanol (3 ml) and conc. ammonia water (1 ml) was stirred for 2 hours at ambient temperature, poured into brine, extracted with ethyl acetate, dried over magnesium sulfate and concentrated under reduced pressure to give 4-(N-acetyl-tert-butylaminomethyl)-2-(5-hydroxybenzofuran-2-yl)thiazole (0.93 g).

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureAfter being cooled
  3. concentrationthe resulting mixture was concentrated under reduced pressure
  4. stirringA solution of the resulting mixture in methanol (3 ml) and conc. ammonia water (1 ml) was stirred for 2 hours at ambient temperature
  5. additionpoured into brine
  6. extractionextracted with ethyl acetate
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8d1169e494d7418ea7b1ef1677662f99
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

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