Ethanol → Ethyl 8-amino-2,3-dihydro-1,4-benzodioxine-5-carboxylate

HRID 1067273Notes

Reaction equation

HRID 1067273 reaction equation
S(Cl)(Cl)=O.[NH2:5][C:6]1[C:11]2[O:12][CH2:13][CH2:14][O:15][C:10]=2[C:9]([C:16]([OH:18])=[O:17])=[CH:8][CH:7]=1.[CH2:19](O)[CH3:20]>>[NH2:5][C:6]1[C:11]2[O:12][CH2:13][CH2:14][O:15][C:10]=2[C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 24386Thionyl ChlorideHCID 211934708-Amino-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid

Product 1

HCID 15817382Ethyl 8-amino-2,3-dihydro-1,4-benzodioxine-5-carboxylate

Conditions

Temperature
-40 °C

Procedure

23.5 g (0.198 mol) of thionyl chloride are introduced slowly into a 2 1 three-necked round-bottomed flask containing 772 ml of ethanol cooled to −40° C., with stirring, the stirring is continued at this temperature for 1 h, 38.6 g (0.198 mol) of 8-amino-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid dissolved in 100 ml of ethanol are added slowly, over 15 min, and the mixture is allowed to warm to room temperature overnight.

Workup

  1. additionare added slowly, over 15 min
  2. temperatureto warm to room temperature overnight

Sources & evidence

ORD record
ord-a108d9fd0230480ab3e8f9c06dfca9ad
Source dataset
uspto-grants-2001_06
Patent number
US06248757B1

Reaction notes

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