Trifluoroacetic anhydride → (4-Oxo-4,10-dihydro-9-oxa-3-thiabenzo[f]azulen-6-ylsulfanyl)acetic acid

HRID 389029Notes

Reaction equation

HRID 389029 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[C:14]([CH2:17][S:18][C:19]1[CH:34]=[CH:33][C:22]([O:23][CH2:24][C:25]2[CH:29]=[CH:28][S:27][C:26]=2[C:30]([OH:32])=O)=[CH:21][CH:20]=1)([OH:16])=[O:15]>ClC(Cl)C>[O:32]=[C:30]1[C:33]2[CH:34]=[C:19]([S:18][CH2:17][C:14]([OH:16])=[O:15])[CH:20]=[CH:21][C:22]=2[O:23][CH2:24][C:25]2[CH:29]=[CH:28][S:27][C:26]1=2

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 684864633-(4-Carboxymethylsulfanylphenoxymethyl)thiophene-2-carboxylic acid

Product 1

HCID 68488427(4-Oxo-4,10-dihydro-9-oxa-3-thiabenzo[f]azulen-6-ylsulfanyl)acetic acidYield 98%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

Trifluoroacetic acid anhydride (28.0 mL, 201 mmol) was added to a dichloroethane (300 mL) solution of the compound obtained in Example 20 (29.0 g, 89 mmol), and the mixture was stirred overnight at 60° C. The solvents were distilled off under a reduced pressure, and water was added to the residue. The precipitated crystals were separated by filtration and dried, to give 26.7 g (98%) of the captioned compound.

Workup

  1. distillationThe solvents were distilled off under a reduced pressure, and water
  2. additionwas added to the residue
  3. customThe precipitated crystals were separated by filtration
  4. customdried

Sources & evidence

ORD record
ord-e6226f7b1b3f418fa429d6c102a15a4c
Source dataset
uspto-grants-2013_02
Patent number
US08377967B2

Reaction notes

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