Thionyl Chloride → HCID 15170044, compound

HRID 1659354Notes

Reaction equation

HRID 1659354 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[O:11][C:10](=[O:13])[C:9]([C:14]([OH:16])=O)=[CH:8]2.S(Cl)([Cl:19])=O>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[O:11][C:10](=[O:13])[C:9]([C:14]([Cl:19])=[O:16])=[CH:8]2

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 2345628-Methoxy-2-oxo-2H-chromene-3-carboxylic acid

Product 1

HCID 15170044HCID 15170044, compound

Procedure

A mixture of 8-methoxycoumarin-3-carboxylic acid (0.66 g) and thionyl chloride (2.5 ml) was heated under reflux for one and half hours. Distilling off the excess thionyl chloride in vacuo gave 8-methoxycoumarin-3-carboxylic acid chloride. Reaction of this product with amoxycillin, 1.257 g, in the same manner as in example 16, yielded D(-)-α-(8-methoxycoumarin-3-carbonamido)-p-hydroxybenzylpenicillin (0.95 g), melting at 187°-9° C. (dec.).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for one and half hours
  3. distillationDistilling off the excess thionyl chloride in vacuo

Sources & evidence

ORD record
ord-a21578e940074044b9c90f98399ba5d8
Source dataset
uspto-grants-1981_12
Patent number
US04303664

Reaction notes

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