Acetyl chloride → HCID 15684563, compound

HRID 728180Notes

Reaction equation

HRID 728180 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[O:7][C:8]2[CH:14]=[C:13]([CH2:15][CH2:16][C:17]3[N:18]=[C:19]4[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][N:20]4[C:26]=3[CH3:27])[CH:12]=[CH:11][C:9]=2[N:10]=1.C(N(CC)CC)C.C(OCC)(=O)C>ClCCl.O1CCCC1>[NH2:5][C:6]1[O:7][C:8]2[CH:14]=[C:13]([CH2:15][CH2:16][C:17]3[N:18]=[C:19]4[CH:24]=[C:23]([O:25][C:1](=[O:3])[CH3:2])[CH:22]=[CH:21][N:20]4[C:26]=3[CH3:27])[CH:12]=[CH:11][C:9]=2[N:10]=1

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 178423694HCID 178423694, compound

Product 1

HCID 15684563HCID 15684563, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Acetyl chloride (1.2 ml) was added to a mixture of 2-amino-6-[2-(7-hydroxy-3-methylimidazo[1,2-a]pyridin-2-yl)ethyl]benzoxazole (1.8 g) and triethylamine (2.4 ml) in dichloromethane (36 ml) under ice-cooling and a mixture was stirred for 15 hours at ambient temperature. To the reaction mixture was added a mixture of ethyl acetate and tetrahydrofuran, and the resulting mixture was washed with water. The mixture was dried over magnesium sulfate and evaporated to give 2-amino-6-[2-(7-acetoxy-3-methylimidazo[1,2-a]pyridin-2-yl)ethyl]benzoxazole (0.27 g).

Workup

  1. temperaturecooling
  2. additionTo the reaction mixture was added
  3. washthe resulting mixture was washed with water
  4. dry with materialThe mixture was dried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-adddb1e9bd35435b80965752766cdb80
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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