Acetyl chloride → HCID 15684669, compound

HRID 728193Notes

Reaction equation

HRID 728193 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]2[N:15]=[C:16]3[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][N:17]3[C:23]=2[CH3:24])=[CH:8][C:7]=1[OH:25].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>CC(C)=O.O.O1CCCC1>[C:1]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]2[N:15]=[C:16]3[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][N:17]3[C:23]=2[CH3:24])=[CH:8][C:7]=1[OH:25])(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 6367Acetyl chlorideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 15684642HCID 15684642, compound

Product 1

HCID 15684669HCID 15684669, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Acetyl chloride (1.5 ml) was dropwise added to a mixture of 2-[2-(4-amino-3-hydroxyphenyl)ethyl]-3,7-dimethylimidazo[1,2-a]pyridine (5.0 g) and sodium bicarbonate (3.0 g) in acetone (30 ml) and water for 10 minutes under ice-cooling and the mixture was stirred for 30 minutes at the same temperature. To the mixture was added a solution of ethyl acetate, tetrahydrofuran and water, and separated organic layer was washed with brine. The mixture was dried over magnesium sulfate and concentrated to give 2-[2-(4-acetamido-3-hydroxyphenyl)ethyl]-3,7-dimethylimidazo[1,2-a]pyridine (3.51 g).

Workup

  1. temperaturecooling
  2. customseparated organic layer
  3. washwas washed with brine
  4. dry with materialThe mixture was dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-79b49dfa0e794328b6252ace262d3c2e
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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