Trifluoroacetic acid → 11-Oxo-2,3,10,11-tetrahydro-1H-benzo[b]indeno[5,6-f] thiepin-7-carboxylic acid

HRID 1731625Notes

Reaction equation

HRID 1731625 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=O)=[C:6]([S:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[CH2:20][CH2:19][CH2:18]3)[CH:5]=1)([OH:3])=[O:2].FC(F)(F)C(O)=O>FC(F)(F)C(OC(=O)C(F)(F)F)=O>[O:13]=[C:11]1[C:23]2[CH:22]=[C:21]3[C:17](=[CH:16][C:15]=2[S:14][C:6]2[CH:5]=[C:4]([C:1]([OH:3])=[O:2])[CH:9]=[CH:8][C:7]=2[CH2:10]1)[CH2:18][CH2:19][CH2:20]3

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 13746688HCID 13746688, compound

Product 1

HCID 1374668911-Oxo-2,3,10,11-tetrahydro-1H-benzo[b]indeno[5,6-f] thiepin-7-carboxylic acid

Reagents, catalysts & solvents 1

HCID 9845Trifluoroacetic anhydrideSolvent

Procedure

4-Carboxy-2-(5-indanylthio)phenylacetic acid (33.55 g, 0.102 mole) was added to trifluoroacetic acid (200 ml) and to the stirred suspension was added, slowly with stirring, trifluoroacetic anhydride (200 ml). After stirring the mixture for 48 hours at room temperature, the mixture was poured slowly onto ice (200 g), and the slurry was diluted to about 1 liter before collecting the crude product. The dried solid was stirred in suspension in acetonitrile for 45 minutes, refiltered and dried to yield 24.95 g.

Workup

  1. additionwas added
  2. stirringAfter stirring the mixture for 48 hours at room temperature
  3. additionthe mixture was poured slowly onto ice (200 g)
  4. additionthe slurry was diluted to about 1 liter
  5. custombefore collecting the crude product
  6. stirringThe dried solid was stirred in suspension in acetonitrile for 45 minutes
  7. customdried
  8. customto yield 24.95 g

Sources & evidence

ORD record
ord-2025782b97374d608bc03578350c0f35
Source dataset
uspto-grants-1986_11
Patent number
US04622403

Reaction notes

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