Sulfuric Acid → Chlorobenzene

HRID 1608001Notes

Reaction equation

HRID 1608001 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[CH:5]1([OH:11])[CH2:10][CH2:9]CCC1.S(=O)(=O)(O)O.[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.NC(N)=[S:26]>O>[CH:1]1([NH:4][C:5](=[O:11])[CH2:10][CH2:9][SH:26])[CH2:23][CH2:18][CH2:19][CH2:3][CH2:2]1.[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 7964ChlorobenzeneHCID 2723790ThioureaHCID 86743397Acrylonitrile cyclohexanol

Product 2

HCID 7964ChlorobenzeneYield 72.4%HCID 14618019N-Cyclohexyl-3-sulfanylpropanamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A pre-mix of acrylonitrile/cyclohexanol (13.3 g/25.1 g) and concentrated sulfuric acid (51.1 g) were added through two addition funnels into a flask containing chlorobenzene (60 g) at 45°-55° C. The mixture was then heated to 60°-70° C. for 3-5 hours and cooled to 20° C. when water (150 g) was added slowly. After 30 minutes stirring, thiourea (19 g) was added and the mixture brought to 60° C. for 1 hour. On cooling to 20° C., caustic (50%, 80 g) was added between 20b 60° C. C under nitrogen and held at 60° C. for 1 hour. The organic layer was separated and washed with warm water to yield 33.9 of N-cyclohexyl-3-mercaptopropionamide in chlorobenzene (72.4% yield).

Workup

  1. additionwere added through two addition funnels into a flask
  2. temperatureThe mixture was then heated to 60°-70° C. for 3-5 hours
  3. additionwas added slowly
  4. waitthe mixture brought to 60° C. for 1 hour
  5. waitC under nitrogen and held at 60° C. for 1 hour
  6. customThe organic layer was separated
  7. washwashed with warm water

Sources & evidence

ORD record
ord-b0211c5cf62d4da48e73c4e5860c546a
Source dataset
uspto-grants-1989_09
Patent number
US04868310

Reaction notes

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