Hydrochloric Acid → HCID 70389796, compound

HRID 1194774Notes

Reaction equation

HRID 1194774 reaction equation
C(OC([NH:6][CH:7]1[CH2:12][S:11][C:10]2[S:13][CH:14]=[CH:15][C:9]=2[CH2:8]1)=O)C.[OH-].[Na+].[ClH:18]>C(O)C(O)C>[ClH:18].[S:13]1[C:10]2[S:11][CH2:12][CH:7]([NH2:6])[CH2:8][C:9]=2[CH:15]=[CH:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 21268845HCID 21268845, compound

Product 1

HCID 70389796HCID 70389796, compound

Reagents, catalysts & solvents 1

HCID 1030Propylene GlycolSolvent

Procedure

A mixture of 5.3 g of 5-ethoxycarbonylamino-5,6-dihydro-4H-thieno[2,3-b]thiopyran, 20 ml of 26% aqueous sodium hydroxide and 20 ml of 1,2-propanediol is heated at 140° for 3 hours. The reaction mixture is cooled and carefully acidified with 29 ml of 6N hydrochloric acid leading to evolution of gas. The resulting mixture is basified with 50% sodium hydroxide solution and extracted with ethyl acetate. The ethyl acetate extract is evaporated to dryness, the residue is dissolved in ether, the ether solution is washed with water and evaporated to dryness. The residue is dissolved in 40 ml of ethyl acetate and 41 ml of a solution of hydrogen chloride in ethyl acetate (0.535 molar) is added. The resulting precipitate is collected and dried to yield 5,6-dihydro-4H-thieno[2,3-b]thiopyran-5-amine hydrochloride.

Workup

  1. temperatureis heated at 140° for 3 hours
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. customis evaporated to dryness
  6. dissolutionthe residue is dissolved in ether
  7. washthe ether solution is washed with water
  8. customevaporated to dryness
  9. dissolutionThe residue is dissolved in 40 ml of ethyl acetate
  10. addition41 ml of a solution of hydrogen chloride in ethyl acetate (0.535 molar) is added
  11. customThe resulting precipitate is collected
  12. customdried

Sources & evidence

ORD record
ord-89519e43cc0b4acbbe3f1250c445abae
Source dataset
uspto-grants-1989_03
Patent number
US04816474

Reaction notes

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