Acetyl chloride → 7-[3-[[(2,3-Dihydro-6-acetoxy-1,4-benzodioxin-2-yl)methyl]amino]propoxy]-2H-1-benzopyran-2-one

HRID 2082466Notes

Reaction equation

HRID 2082466 reaction equation
Cl.[OH:2][C:3]1[CH:29]=[CH:28][C:6]2[O:7][CH:8]([CH2:11][NH:12][CH2:13][CH2:14][CH2:15][O:16][C:17]3[CH:27]=[CH:26][C:20]4[CH:21]=[CH:22][C:23](=[O:25])[O:24][C:19]=4[CH:18]=3)[CH2:9][O:10][C:5]=2[CH:4]=1.[C:30](Cl)(=[O:32])[CH3:31]>C(O)(=O)C>[C:30]([O:2][C:3]1[CH:29]=[CH:28][C:6]2[O:7][CH:8]([CH2:11][NH:12][CH2:13][CH2:14][CH2:15][O:16][C:17]3[CH:27]=[CH:26][C:20]4[CH:21]=[CH:22][C:23](=[O:25])[O:24][C:19]=4[CH:18]=3)[CH2:9][O:10][C:5]=2[CH:4]=1)(=[O:32])[CH3:31]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 197786767-[3-[[(2,3-Dihydro-6-hydroxy-1,4-benzodioxin-2-yl)methyl]amino]propoxy]-2H-1-benzopyran-2-one hydrochloride

Product 1

HCID 197786887-[3-[[(2,3-Dihydro-6-acetoxy-1,4-benzodioxin-2-yl)methyl]amino]propoxy]-2H-1-benzopyran-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7-[3-[[(2,3-Dihydro-6-hydroxy-1,4-benzodioxin-2-yl)methyl]amino]propoxy]-2H-1-benzopyran-2-one hydrochloride (0.10 g, 0.24 mmole), prepared as in example 5 above, was dissolved in 50 ml of glacial acetic acid and 3.05 ml (43 mmole) of acetyl chloride added in portions over a 30 minute period, during which the reaction mixture was gently warmed with a heat gun. The solvent and excess reagent were then removed in vacuum and diethyl ether added. Upon standing overnight, 0.030 g of the title compound as a monohydrochloride, m.p. 175° C., crystallized.

Workup

  1. temperaturewas gently warmed with a heat gun
  2. customThe solvent and excess reagent were then removed in vacuum and diethyl ether
  3. additionadded
  4. custom0.030 g of the title compound as a monohydrochloride, m.p. 175° C., crystallized

Sources & evidence

ORD record
ord-abf2cf687791424eac3ae656cf5f1627
Source dataset
uspto-grants-1993_02
Patent number
US05189171

Reaction notes

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