Thionyl Chloride → 2-AMino-N-(2,3-dihydro-benzo[1,4]dioxin-6-ylMethyl)-acetaMide

HRID 1725398Notes

Reaction equation

HRID 1725398 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11]O)[C:5]=2[O:4][CH2:3][CH2:2]1.S(Cl)([Cl:15])=O>ClCCl>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][Cl:15])[C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 27761822,3-dihydro-1,4-benzodioxin-5-ylmethanol

Product 1

HCID 224188622-AMino-N-(2,3-dihydro-benzo[1,4]dioxin-6-ylMethyl)-acetaMideYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve (2,3-Dihydrobenzo[1,4]dioxin-5-yl)methanol (1.8 g, 10.8 mmol) in dichloromethane (15 mL). Add neat thionyl chloride (2 mL, 27.4 mmol) dropwise to the stirring reaction mixture at 25° C. under nitrogen. Stir the reaction for 15 minutes and concentrate under reduced pressure to obtain 2.0 g (100%) of the desired compound as a yellow oil.

Workup

  1. customdropwise to the stirring reaction mixture at 25° C. under nitrogen
  2. customthe reaction for 15 minutes
  3. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-6a8f258d86aa44a7b44a262961146e42
Source dataset
uspto-grants-2009_02
Patent number
US07491716B2

Reaction notes

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