Propionyl chloride → HCID 21268840, compound

HRID 1194778Notes

Reaction equation

HRID 1194778 reaction equation
Cl.[S:2]1[C:6]2[S:7][CH2:8][CH:9]([NH2:11])[CH2:10][C:5]=2[CH:4]=[CH:3]1.C(N(C(C)C)C(C)C)C.[C:21](Cl)(=[O:24])[CH2:22][CH3:23]>C(Cl)Cl>[C:21]([NH:11][CH:9]1[CH2:8][S:7][C:6]2[S:2][CH:3]=[CH:4][C:5]=2[CH2:10]1)(=[O:24])[CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 70389796HCID 70389796, compound

Product 1

HCID 21268840HCID 21268840, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 8.31 g of 5,6-dihydro-4H-thieno[2,3-b]- thiopyran-5-amine hydrochloride, 17.4 ml of ethyldiisopropylamine, 4.07 g of propionyl chloride in 80 ml of methylene chloride is kept for 30 minutes at room temperature. The reaction mixture is washed with 1N hydrochloric acid and then with saturated sodium bicarbonate solution, the organic layer is dried over magnesium sulfate and the solvent is removed in vacuo to yield N-propionyl-5,6-dihydro-4H-thieno[2,3-b]-thiopyran-5-amine. This is refluxed for 3 hours with 85 ml of 1M borane in tetrahydrofuran. Water and 3N hydrochloric acid are added and the mixture is heated briefly. Basification of the aqueous layer followed by extraction with ether affords an oil after removal of solvent. Addition of ethanolic hydrochloric acid affords N-propyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-5-amine hydrochloride, m.p. 107°-110°.

Workup

  1. washThe reaction mixture is washed with 1N hydrochloric acid
  2. dry with materialwith saturated sodium bicarbonate solution, the organic layer is dried over magnesium sulfate
  3. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-d10e17ee35d54fff954591aa5cbb96dc
Source dataset
uspto-grants-1989_03
Patent number
US04816474

Reaction notes

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