HCID 13472255, compound → HCID 13472256, compound

HRID 1789132Notes

Reaction equation

HRID 1789132 reaction equation
CC([NH:5][S:6]([C:9]1[C:17]2[CH2:16][S:15][CH2:14][C:13]=2[CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7])(C)C>FC(F)(F)C(O)=O.CCCCCC.C(OCC)(=O)C>[CH2:14]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]([S:6]([NH2:5])(=[O:7])=[O:8])[C:17]=2[CH2:16][S:15]1

Participants

4

Reactant 1

HCID 13472255HCID 13472255, compound

Product 1

HCID 13472256HCID 13472256, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A solution of 3.0 g of 1,3-dihydro-N-(1,1-dimethylethyl)benzo[c]thiophene-4-sulfonamide in 50 ml of trifluoroacetic acid was stirred at ambient temperature for 4 hours. The brown solution was concentrated in vacuo. 1-Chlorobutane was added to the resulting brown oil and the mixture concentrated in vacuo. Repeating this procedure gave an oil which on trituration with 1-chlorobutane gave a brown solid. Purification of the crude reaction product by chromatography, using hexane/ethyl acetate (3:2) as eluent gave 1.4 g of 1,3-dihydrobenzo[c]thiophene-4-sulfonamide as a pale yellow solid, m.p. 146°-148°.

Workup

  1. concentrationThe brown solution was concentrated in vacuo
  2. addition1-Chlorobutane was added to the resulting brown oil
  3. concentrationthe mixture concentrated in vacuo
  4. customRepeating this procedure gave an oil which on trituration with 1-chlorobutane
  5. customgave a brown solid
  6. customPurification of the crude
  7. customreaction product by chromatography

Sources & evidence

ORD record
ord-c00937995bdd4e3994a23e4c6555f433
Source dataset
uspto-grants-1987_08
Patent number
US04687508

Reaction notes

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