Hydrochloric Acid → 2-(Phenylsulfanyl)ethyl nitroacetate

HRID 259298Notes

Reaction equation

HRID 259298 reaction equation
[C:1]1([S:7][CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[N+:12]([CH2:15][C:16]([O-])=[O:17])([O-:14])=[O:13]>ClCCl>[N+:12]([CH2:15][C:16]([O:10][CH2:9][CH2:8][S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:17])([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 43580NitroacetateHCID 696852-(Phenylthio)ethanol

Product 1

HCID 214241702-(Phenylsulfanyl)ethyl nitroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was prepared according to a known process (British Pat. No. 835,521 Spec.). Namely, a solution of β-phenylthioethylalcohol (50g) in dichloromethane (15ml) was saturated with dry hydrogen chloride at 0° C. and to the resulting solution was added, in three portions, dipottassium nitroacetate (27.5g). During the addition, hydrogen chloride was passed into the well stirred mixture while the temperature was allowed to rise to 10° C. Then the gas supply was stopped and the reaction mixture was stirred for 4 hours at less than 10° C. After stirring for 20 hours at 0° C., excess β-phenylthioethyl-alcohol was removed under reduced pressure and the remaining solution was kept to cool, the crystals precipitated was washed with water and then with n-hexane, giving β-phenylthioethyl nitroacetate (11.1g), m.p. 22.0°-24.0° C..

Workup

  1. customThis compound was prepared
  2. customto rise to 10° C
  3. stirringthe reaction mixture was stirred for 4 hours at less than 10° C
  4. stirringAfter stirring for 20 hours at 0° C.
  5. customexcess β-phenylthioethyl-alcohol was removed under reduced pressure
  6. temperatureto cool
  7. customthe crystals precipitated
  8. washwas washed with water

Sources & evidence

ORD record
ord-4895b88eeaa04b3492b1e54d4b3e7ddb
Source dataset
uspto-grants-1977_07
Patent number
US04036984

Reaction notes

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