Ethanethiol → HCID 20072961, compound

HRID 704594Notes

Reaction equation

HRID 704594 reaction equation
C[O-].[Na+].[CH2:4]([SH:6])[CH3:5].[CH3:7][O:8][C:9]1[CH:25]=[CH:24][C:12]([O:13][CH2:14][CH:15]2[N:19]([C:20](=[O:23])[CH2:21]Cl)[CH2:18][CH2:17][S:16]2)=[CH:11][CH:10]=1>CO>[CH3:7][O:8][C:9]1[CH:25]=[CH:24][C:12]([O:13][CH2:14][CH:15]2[N:19]([C:20](=[O:23])[CH2:21][S:6][CH2:4][CH3:5])[CH2:18][CH2:17][S:16]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 10402623HCID 10402623, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 20072961HCID 20072961, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 0.56 g of sodium methylate is MeOH (5 ml), cooled at 0° C., was treated with 0,71 ml of ethanethiol (CH3CH2SH). After 10 minutes, a solution of 3 g of 2-(4-methoxyphenoxymethyl)-3-α-chloroacetyl-1,3-thiazolidine in 10 ml MeOH was dropped into the mixture. After 30 minutes, the solvent was removed under reduced pressure and the residue was partitioned between 30% NaH2PO4 and ethyl acetate. The organic phase was washed with water, dried over Na2SO4 and concentrated to dryness to yield 2,9 g of 2-(4-methoxyphenoxymethyl)-3-ethylmercaptoacetyl- 1,3-thiazolidine after crystallization from isopropyl ether, m.p. 98°-110° C.

Workup

  1. waitAfter 30 minutes
  2. customthe solvent was removed under reduced pressure
  3. customthe residue was partitioned between 30% NaH2PO4 and ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-66438709f87648e297d9ba2eabe96081
Source dataset
uspto-grants-1991_01
Patent number
US04988701

Reaction notes

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