Thionyl Chloride → HCID 86739952, compound

HRID 2164234Notes

Reaction equation

HRID 2164234 reaction equation
[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][C:18]([OH:20])=O)=[CH:16][C:3]1=2.S(Cl)([Cl:23])=O>>[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][C:18]([Cl:23])=[O:20])=[CH:16][C:3]1=2

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 12789591HCID 12789591, compound

Product 1

HCID 86739952HCID 86739952, compound

Procedure

2.68 g of (11-oxo-2-dibenz[b,f]oxepinyl)acetic acid is dissolved in 9.15 ml of thionyl chloride and heated for 3 hours under reflux. The mixture is then concentrated under vacuum, thus obtaining 3.04 g of (11-oxo-2-dibenz[b,f]oxepinyl)acetyl chloride. This acid chloride is reacted under the conditions of Example 2 with trimethyl phosphite, yielding 1.34 g of 2-(11-oxo-2-dibenz[b,f]oxepinyl)-1-hydroxyethenephosphonic acid dimethyl ester, mp 118° C. The resultant product is reacted with dimethyl phosphite as described in Example 1, yielding the 2-(11-oxo-2-dibenz[b,f]oxepinyl)-1-hydroxyethane-1,1-bis(phosphonic acid dimethyl ester), mp 133° C.

Workup

  1. temperatureheated for 3 hours
  2. temperatureunder reflux
  3. concentrationThe mixture is then concentrated under vacuum

Sources & evidence

ORD record
ord-69faa7fb4215477aa2cb44546e96a75c
Source dataset
uspto-grants-1985_03
Patent number
US04503049

Reaction notes

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