Ammonia → (3-Phenoxyphenyl)methanethiol

HRID 904224Notes

Reaction equation

HRID 904224 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NC(N)=[S:18].N.Cl>C(O)(C)C.O>[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][SH:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 2723790Thiourea

Product 1

HCID 14350403(3-Phenoxyphenyl)methanethiol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 30.8 g of m-phenoxybenzyl bromide in 70 ml of isopropanol is reacted with 9.5 g of thiourea in 30 ml of water and the reaction mixture is refluxed briefly. After cooling, 25 ml of a 25% ammonia solution are added and the mixture is heated briefly to reflux and then allowed to cool, whereupon it is acidified with 18% hydrochloric acid and extracted with methylene chloride. The extract is dried over magnesium sulfate and concentrated, affording the compound of the formula ##STR7## with a boiling point of 114°-116° C.'0.05 mm Hg.

Workup

  1. temperaturethe reaction mixture is refluxed briefly
  2. temperatureAfter cooling
  3. temperaturethe mixture is heated briefly
  4. temperatureto reflux
  5. temperatureto cool, whereupon it
  6. extractionextracted with methylene chloride
  7. dry with materialThe extract is dried over magnesium sulfate
  8. concentrationconcentrated
  9. customaffording the compound of the formula ##STR7## with a boiling point of 114°-116° C.'0.05 mm Hg

Sources & evidence

ORD record
ord-831aadc55eac44c3a9dbf72ef047fd26
Source dataset
uspto-grants-1980_10
Patent number
US04230722

Reaction notes

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