Hydrochloric Acid → 4,5,6,7-Tetrahydro-7-oxobenzo[b]thiophen-4-amine hydrochloride

HRID 259336Notes

Reaction equation

HRID 259336 reaction equation
[O:1]=[C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]([NH:11]C=O)[CH2:4][CH2:3]1.[ClH:14]>C(O)C>[ClH:14].[O:1]=[C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]([NH2:11])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23347790N-(7-Oxo-4,5,6,7-tetrahydro-1-benzothiophen-4-yl)formamide

Product 1

HCID 233477954,5,6,7-Tetrahydro-7-oxobenzo[b]thiophen-4-amine hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (+)-N-(4,5,6,7-tetrahydro-7-oxobenzo[b]thien-4-yl)formamide (52.65 grams) in 525 ml. of 95% ethanol and 525 ml. of 2N HCl is heated at reflux for 2 hours. The mixture is cooled, filtered through glass wool and the filtrate is evaporated to dryness. The dark solid is dissolved in 180 ml. of water and the insoluble material is collected by filtration. The filter cake is washed with 70 ml. of water and the combined solution containing the title compound is used in the next operation. A 3 ml. solution is evaporated to dryness and the residue is dissolved in 95% ethanol. The ethanol solution is decolorized with activated carbon and filtered. The filtrate is evaporated to dryness to afford 0.5 grams of the title compound, m.p. 212°-214° C. (dec.), [α]D26 = + 13.56° (c, 0.59 in methanol).

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureThe mixture is cooled
  3. filtrationfiltered through glass wool
  4. customthe filtrate is evaporated to dryness
  5. dissolutionThe dark solid is dissolved in 180 ml
  6. filtrationof water and the insoluble material is collected by filtration
  7. washThe filter cake is washed with 70 ml
  8. additionof water and the combined solution containing the title compound
  9. customsolution is evaporated to dryness
  10. dissolutionthe residue is dissolved in 95% ethanol
  11. filtrationfiltered
  12. customThe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-65f9a4dd961149b893cec5e0b18b340c
Source dataset
uspto-grants-1977_07
Patent number
US04036979

Reaction notes

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