Ethanethiol → HCID 20483196, compound

HRID 647762Notes

Reaction equation

HRID 647762 reaction equation
[H-].[Na+].C(S)C.C[O:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][CH:12]([N:18]([CH2:22][CH2:23][CH2:24][S:25][CH3:26])[CH2:19][CH2:20][CH3:21])[CH2:13]2>CN(C)C=O>[OH:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][CH:12]([N:18]([CH2:22][CH2:23][CH2:24][S:25][CH3:26])[CH2:19][CH2:20][CH3:21])[CH2:13]2

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 20483194HCID 20483194, compound

Product 1

HCID 20483196HCID 20483196, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1 g sodium hydride in 40 g dimethylformamide is treated at 0° with 3.3 ml ethylmercaptan. 4.5 g 1,2,3,4-tetrahydro-5-methoxy-2-[N-(3-methylthiopropyl)-N-propylamino]-naphthalene in 30 ml dimethylformamide are added. The reaction mixture is stirred for 20 hours at 120°, cooled, concentrated and partitioned between ether and 2 N hydrochloric acid. The aqueous phase is adjusted to pH 11 at 5° and extracted with methylene chloride. The organic phase is dried, filtered and concentrated to give the crude title compound, which is converted into the hydrogen fumarate in isopropanol/pentane. M.pt. sintering from 70° (from ethanol/ether). The starting material may be obtained as follows:

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. custompartitioned between ether and 2 N hydrochloric acid
  4. customis adjusted to pH 11 at 5°
  5. extractionextracted with methylene chloride
  6. customThe organic phase is dried
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9faf13f3715f4b78937be4ad902d64d8
Source dataset
uspto-grants-1983_10
Patent number
US04410519

Reaction notes

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