Methyl 5-bromovalerate → Phenytoin

Reaction equation

[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:11][C:10](=[O:12])[NH:9][C:8]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].BrCCCCC(OC)=O>>[CH:17]1[CH:18]=[CH:19][C:14]([C:7]2([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[NH:11][C:10]([OH:12])=[N:9][C:8]2=[O:13])=[CH:15][CH:16]=1

Participants

Reactant 2

HCID 79557Methyl 5-bromovalerate

HCID 97955475,5-Diphenylhydantoin sodium

Product 1

HCID 1775Phenytoin

Procedure

Following the method of Cook et al, Res. Comm. Chem. Path. Pharm. 5:767(1973), sodium diphenylhydantoin is reacted with methyl 5-bromovalerate followed by acid hydrolysis to yield the following: ##STR15##

Workup

customfollowed by acid hydrolysis
customto yield the following: ##STR15##

Sources & evidence

ORD record: ord-05ced917aa254317b64d4bc091a33dff
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04225485

Reaction notes

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