Ethanol → O-Ethyl (3-Chlorophenyl)-thiocarbamate

HRID 223395

Reaction equation

HRID 223395 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]=[C:9]=[S:10])[CH:5]=[CH:6][CH:7]=1.N1C2C(=CC=CC=2)C=CC=1.[CH2:21]([OH:23])[CH3:22]>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[S:10])[O:23][CH2:21][CH3:22])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 7047QuinolineHCID 754493-Chlorophenyl isothiocyanate

Product 1

HCID 54084842O-Ethyl (3-Chlorophenyl)-thiocarbamate

Procedure

A mixture of 45.5 gm (0.268 mol) of 3-chlorophenylisothiocyanate, 200 ml of anhydrous ethanol and 1 ml of quinoline was refluxed for 48 hours. Then, the reaction mixture was evaporated in an aspirator vacuum, the residue was taken up in ether, and the resulting solution was washed first with 5% hydrochloric acid and then thoroughly with water, dried, and evaporated again. After recrystallization from methanol/water, 49.5 gm (86% of theory) of colorless crystals with a melting point of 78°-79° C. were obtained.

Workup

  1. temperaturewas refluxed for 48 hours
  2. customThen, the reaction mixture was evaporated in an aspirator vacuum
  3. washthe resulting solution was washed first with 5% hydrochloric acid
  4. dry with materialthoroughly with water, dried
  5. customevaporated again
  6. customAfter recrystallization from methanol/water, 49.5 gm (86% of theory) of colorless crystals with a melting point of 78°-79° C.
  7. customwere obtained

Sources & evidence

ORD record
ord-0314404d9a3246f4a990bc889874e10e
Source dataset
uspto-grants-1982_10
Patent number
US04353919

Linked notes

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