Toluene → HCID 21268838, compound

HRID 1194775Notes

Reaction equation

HRID 1194775 reaction equation
[OH-].[Na+].Cl.[S:4]1[C:8]2[S:9][CH2:10][CH:11]([NH2:13])[CH2:12][C:7]=2[CH:6]=[CH:5]1.[CH2:14](I)[CH2:15][CH3:16].[C:18]1(C)[CH:23]=CC=C[CH:19]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:14]([N:13]([CH2:19][CH2:18][CH3:23])[CH:11]1[CH2:10][S:9][C:8]2[S:4][CH:5]=[CH:6][C:7]=2[CH2:12]1)[CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 336431-IodopropaneHCID 70389796HCID 70389796, compound

Product 1

HCID 21268838HCID 21268838, compound

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

Sodium hydroxide solution (50%, 700 ml) is added in portions to a mixture of 114.65 g of 5,6-dihydro-4H-thieno[2,3-b]thiopyran-5-amine hydrochloride, 940 g of n-propyl iodide and 18.3 g of tetra-n-butylammonium bromide in 700 ml of toluene. The reaction mixture is heated under reflux at 100° for 20 hours. The organic layer is separated and the aqueous phase is extracted with 300 ml of toluene. The combined toluene extracts are washed with water dried and concentrated under vacuo (so as to remove any remaining n-propyl iodide). The residue is then distilled under high vacuum to obtain N,N-dipropyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-5-amine, b.p. 155°/0.5 mm Hg.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux at 100° for 20 hours
  3. customThe organic layer is separated
  4. extractionthe aqueous phase is extracted with 300 ml of toluene
  5. washThe combined toluene extracts are washed with water
  6. customdried
  7. concentrationconcentrated under vacuo (so as
  8. customto remove any remaining n-propyl iodide)
  9. distillationThe residue is then distilled under high vacuum

Sources & evidence

ORD record
ord-c7086ba2c6b84bf5895276ec27e64aaa
Source dataset
uspto-grants-1989_03
Patent number
US04816474

Reaction notes

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