Methanethiol → HCID 86735331, compound

HRID 1833446Notes

Reaction equation

HRID 1833446 reaction equation
[CH3:1][SH:2].[CH3:3][O-:4].[Na+].[Na].Br[CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19](OC)=O)[C:9]([O:11][CH3:12])=[O:10]>CO>[CH3:19][CH:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:8][C:9]([O:11][CH3:12])=[O:10])[C:1]([O:4][CH3:3])=[S:2]

Participants

6

Reactant 4

HCID 878MethanethiolHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 12760707Dimethyl 2-bromononanedioate

Product 1

HCID 86735331HCID 86735331, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl mercaptan (excess) is passed into a rapidly stirred solution of sodium methoxide (13.5 g., 0.25 mole) in dry methanol (200 ml.) at 0° C. to generate sodium methylmercaptide. The resulting solution is treated with dimethyl 2-bromoazelate (55.0 g., 0.186 mole), then stirred and heated at reflux under nitrogen for 5 hours. The reaction solution is concentrated in vacuo, diluted with ether and filtered. The filtrate is washed with water (until the washings are neutral), dried over sodium sulfate and distilled providing the title compound as a colorless liquid (28.4 g., 58%), bp 0.2 mm 128°-138° C.; pmr (CDCl3) δ 2.10 (s, 3H), 2.31 (t,2H), 3.20 (t,H), 3.63 (s,3H) and 3.71 (s, 3H).

Workup

  1. temperatureheated
  2. temperatureat reflux under nitrogen for 5 hours
  3. concentrationThe reaction solution is concentrated in vacuo
  4. additiondiluted with ether
  5. filtrationfiltered
  6. washThe filtrate is washed with water (until the washings
  7. dry with materialdried over sodium sulfate
  8. distillationdistilled

Sources & evidence

ORD record
ord-c837aa430c5348f6a00c56717078471f
Source dataset
uspto-grants-1978_01
Patent number
US04066675

Reaction notes

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