Methanethiol → HCID 13672738, compound

HRID 543036Notes

Reaction equation

HRID 543036 reaction equation
C[O-].[Na+].[Na].[CH3:5][SH:6].Cl[C:8]1[N:13]=[C:12]([CH:14]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[CH:10][CH:9]=1>CS(C)=O.CO>[CH3:5][S:6][C:8]1[N:13]=[C:12]([CH:14]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 878MethanethiolHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 12833242HCID 12833242, compound

Product 1

HCID 13672738HCID 13672738, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Conditions

Temperature
13 °C

Procedure

To a mixture of sodium methoxide (made from 100 ml (2.47 m) of methanol and 1.50 g (0.652 m) of sodium metal) which had been cooled to 13° C. was added 7.0 ml (0.126 m) of methylmercaptan. The mixture was allowed to warm to room temperature and then 20.0 g of 6-chloro-2-(diphenoxymethyl)pyridine and 150 ml of dimethylsulfoxide was added thereto. The mixture was heated to 90° C. and after 4 days at this temperature, the reaction mixture was cooled to room temperature and poured into 300 ml of ice. The solution was extracted with methylene chloride and the extract was dried over magnesium sulfate and the solvent stripped off under reduced pressure. The residue was further purified using preparative high pressure liquid chromatography with a 2:98 mixture of ethylacetate and hexane. The oil thus obtained crystallized in n-hexane and was purified by recrystallization from n-hexane leaving the above named compound as a white solid in a yield of 49 g (98 percent pure). The product melted at 58°-59° C. and its structure was confirmed by its NMR spectrum. Upon analysis, the product was found to have carbon, hydrogen and nitrogen contents of 70.42, 5.19 and 4.20 percent, respectively, as compared with the theoretical contents of 70.59, 5.26 and 4.33 percent, respectively, as calculated for the above named compound (Compound 3).

Workup

  1. temperatureto warm to room temperature
  2. temperatureThe mixture was heated to 90° C. and after 4 days at this temperature
  3. temperaturethe reaction mixture was cooled to room temperature
  4. extractionThe solution was extracted with methylene chloride
  5. dry with materialthe extract was dried over magnesium sulfate
  6. customThe residue was further purified
  7. additionwith a 2:98 mixture of ethylacetate and hexane
  8. customThe oil thus obtained
  9. customcrystallized in n-hexane
  10. customwas purified by recrystallization from n-hexane leaving the

Sources & evidence

ORD record
ord-ebbc0aa0f58f48cd920d845e2e48111e
Source dataset
uspto-grants-1987_04
Patent number
US04661144

Reaction notes

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