Ketoprofen → HCID 131725382, compound

HRID 1743979Notes

Reaction equation

[C:1]1([CH:7]([CH3:11])[C:8]([Cl:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OC(C([C:17]1[CH:30]=[CH:29][CH:28]=[C:19]([C:20](C2C=CC=CC=2)=[O:21])[CH:18]=1)C)=O.S(Cl)(Cl)=O.[Cl-].[OH:36][C:37]([CH:39]([C:41]1[CH:54]=[CH:53][CH:52]=[C:43]([C:44]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[O:45])[CH:42]=1)[CH3:40])=[O:38]>>[C:20]([C:3]1[CH:2]=[C:1]([CH:7]([CH3:11])[C:8]([Cl:10])=[O:9])[CH:6]=[CH:5][CH:4]=1)(=[O:21])[C:19]1[CH:28]=[CH:29][CH:30]=[CH:17][CH:18]=1.[OH:38][C:37]([CH:39]([C:41]1[CH:54]=[CH:53][CH:52]=[C:43]([C:44]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)=[O:45])[CH:42]=1)[CH3:40])=[O:36]

Participants

Reactant 4

HCID 3825Ketoprofen

HCID 24386Thionyl Chloride

HCID 2760403Hydratropoyl chloride

HCID 22236856HCID 22236856, compound

Product 1

HCID 131725382HCID 131725382, compoundYield 99%

Procedure

The procedure is identical to that for the synthesis of α-phenylpropionic acid chloride. Starting with 4.69 g (M=254.3 g, 18.4 mmol) of ketoprofen and 13.4 ml (10 eq) of thionyl chloride, 5.26 g (M=272.8 g, 18.2 mmol) of ketoprofen chloride are obtained, i.e. a yield of 99%.

Workup

customare obtained

Sources & evidence

ORD record: ord-98b191af8b7f4d53843902db1ff36101
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07012138B1

Reaction notes

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