Ammonia → [4-(Prop-2-en-1-yloxy)phenyl]methanethiol

HRID 33490Notes

Reaction equation

HRID 33490 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11]Cl)=[CH:7][CH:6]=1)[CH:2]=[CH2:3].NC(N)=[S:15].O.N>C(O)C>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][SH:15])=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 2723790ThioureaHCID 123479361-Allyloxy-4-chloromethyl-benzene

Product 1

HCID 22242087[4-(Prop-2-en-1-yloxy)phenyl]methanethiolYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 2.00 g (10.9 mmol) 1-allyloxy-4-chloromethyl-benzene and 917 mg (12.1 mmol) thiourea in 3.0 ml ethanol was heated to reflux for 7 h. Solvents were distilled off and the crystalline residue was washed with cold ethanol and isolated by filtration. After addition of 2.5 ml ethanol, 1.0 ml water and 0.7 ml 25% aqueous ammonia, the mixture was heated to reflux for 1 h. Ethanol was distilled off, then acidified with 0.5 ml half conc. HCl and extracted with ethyl acetate. The solution was dried over MgSO4 and solvents were removed in vacuo to yield 1.59 g (81%) colorless oil, which was used immediately.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 7 h
  3. distillationSolvents were distilled off
  4. washthe crystalline residue was washed with cold ethanol
  5. customisolated by filtration
  6. temperaturethe mixture was heated
  7. temperatureto reflux for 1 h
  8. distillationEthanol was distilled off
  9. extractionextracted with ethyl acetate
  10. dry with materialThe solution was dried over MgSO4 and solvents
  11. customwere removed in vacuo

Sources & evidence

ORD record
ord-70d7487da8084e27bd9cb2a255ecb9de
Source dataset
uspto-grants-2008_09
Patent number
US07429605B2

Reaction notes

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