Diazomethane → methyl 10-Oxo-8-fluoro-dibenzo [b,f]thiepin-3-carboxylate

HRID 1156153Notes

Reaction equation

HRID 1156153 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:7]=2[S:6][C:5]2[CH:14]=[C:15]([C:18]([OH:20])=[O:19])[CH:16]=[CH:17][C:4]=2[CH2:3]1.[N+](=[CH2:23])=[N-]>CO.CCOCC>[O:1]=[C:2]1[C:8]2[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:7]=2[S:6][C:5]2[CH:14]=[C:15]([C:18]([O:20][CH3:23])=[O:19])[CH:16]=[CH:17][C:4]=2[CH2:3]1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 1303510610-Oxo-8-fluoro-dibenzo[b,f]thiepin-3-carboxylic acid

Product 1

HCID 13035107methyl 10-Oxo-8-fluoro-dibenzo [b,f]thiepin-3-carboxylateYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

10-Oxo-8-fluoro-dibenzo[b,f]thiepin-3-carboxylic acid (2 g; 6.94 mmoles) is partially dissolved in methanol (20 mL) and is treated with excess diazomethane in ether. The resulting solution is evaporated to dryness, triturated in methanol to yield 1.98 g (94%) of methyl 10-Oxo-8-fluoro-dibenzo [b,f]thiepin-3-carboxylate, m.p. 129°-131° C.

Workup

  1. customThe resulting solution is evaporated to dryness
  2. customtriturated in methanol

Sources & evidence

ORD record
ord-66aae2deff6345efb79dd06b0b1fcb92
Source dataset
uspto-grants-1982_06
Patent number
US04334077

Reaction notes

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