Acetyl chloride → HCID 54391225, compound

HRID 361345

Reaction equation

HRID 361345 reaction equation
[CH2:1]([N:3]([CH2:14][CH3:15])[C:4]([O:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[NH2:13])=[O:5])[CH3:2].CCN(CC)CC.[C:23](Cl)(=[O:25])[CH3:24].C(OCC)(=O)C.CCCCC>C(Cl)Cl>[CH2:14]([N:3]([CH2:1][CH3:2])[C:4]([O:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[NH:13][C:23](=[O:25])[CH3:24])=[O:5])[CH3:15]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 22335286Ethyl acetate pentaneHCID 543040194-Aminopyridin-3-yl diethylcarbamate

Product 1

HCID 54391225HCID 54391225, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Amino-3-pyridinol N,N-diethylcarbamate (4.18 g) was dissolved in CH2Cl2 (75 mL) containing Et3N (2.22 g). The reaction mixture was chilled in an ice-water bath and then acetyl chloride (1.57 g) was added dropwise. After stirring in the cold bath for 15 minutes, the mixture was concentrated under reduced pressure to a volume of ca. 20 mL. This suspension was applied directly to a flash chromatography column and eluted with 5% Et3N/ethyl acetate. The product-containing fractions were concentrated to give 3.76 g of chromatographically pure product. An analytically pure material was obtained by recrystallization from ethyl acetate/pentane, m.p. 102°-104° C.

Workup

  1. temperatureThe reaction mixture was chilled in an ice-water bath
  2. concentrationthe mixture was concentrated under reduced pressure to a volume of ca. 20 mL
  3. washeluted with 5% Et3N/ethyl acetate
  4. concentrationThe product-containing fractions were concentrated
  5. customto give 3.76 g of chromatographically pure product

Sources & evidence

ORD record
ord-5edb993134624c18a07073ec72ba97d3
Source dataset
uspto-grants-1999_02
Patent number
US05866565

Linked notes

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