Ethanethiol → 2-Mercaptoethyl-5-nitrophenyl hydroxyethyl sulfone

HRID 981812Notes

Reaction equation

HRID 981812 reaction equation
[OH:1][CH2:2][CH2:3][S:4]([C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1Cl)(=[O:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:23]([SH:25])[CH3:24]>>[OH:1][CH2:2][CH2:3][S:4]([C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[CH2:24][CH2:23][SH:25])(=[O:6])=[O:5]

Participants

4

Reactant 3

HCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 136286432-Chloro-5-nitrophenyl hydroxyethyl sulfone

Product 1

HCID 538699932-Mercaptoethyl-5-nitrophenyl hydroxyethyl sulfoneYield 91.5%

Procedure

132.85 g of 2-chloro-5-nitrophenyl hydroxyethyl sulfone are suspended together with 69.1 g of potassium carbonate in 500 ml of ethylmercaptan, and the reaction is allowed to proceed at 30° C. for 2 hours. The ethylmercaptan excess is distilled off under a high vacuum, the residue is taken up in ethanol, and the product is crystallized by pouring into ice-water. After filtration this gives 140.5 g of 2-mercaptoethyl-5-nitrophenyl hydroxyethyl sulfone having a melting of 112°-114° C. (purity >95%), which corresponds to a yield of 91.5% of theory, relative to starting 2-chloro-5-nitrophenyl hydroxyethyl sulfone.

Workup

  1. distillationThe ethylmercaptan excess is distilled off under a high vacuum
  2. customthe product is crystallized
  3. additionby pouring into ice-water
  4. filtrationAfter filtration this gives 140.5 g of 2-mercaptoethyl-5-nitrophenyl hydroxyethyl sulfone having a melting of 112°-114° C. (purity >95%), which

Sources & evidence

ORD record
ord-7f9a24e62c7b4130993bf65864dc705d
Source dataset
uspto-grants-1991_02
Patent number
US04992589

Reaction notes

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