Hydrochloric Acid → (3-Chloro-4-methoxyphenyl)methanethiol

HRID 1097345Notes

Reaction equation

HRID 1097345 reaction equation
N[C:2](N)=[S:3].[Cl:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])CBr.[OH-].[Na+].Cl>C(O)C.C(OCC)C>[Cl:5][C:6]1[CH:7]=[C:8]([CH2:2][SH:3])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 114703704-(Bromomethyl)-2-chloro-1-methoxybenzene

Product 1

HCID 12347049(3-Chloro-4-methoxyphenyl)methanethiolYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

Thiourea (3.04 g, 0.04 mol) was added to a solution of 3-chloro-4-methoxybenzyl bromide (4.0 g, 0.02 mol) in ethanol (200 ml) and refluxed for 16 hours. The reaction mixture was concentrated in vacuo and the residue was subsequently dissolved in aqueous sodium hydroxide solution (30 g, 0.75 mol in 300 ml water) and heated at 80° C. for one hour. The reaction mixture was cooled with an ice bath and acidified by addition of concentrated hydrochloric acid. The product was isolated by extraction three times into diethyl ether. The combined organic phases were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo, to give the subtitle compound as a colourless oil in 83% yield (3.0 g).

Workup

  1. temperaturerefluxed for 16 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. temperatureThe reaction mixture was cooled with an ice bath
  4. dry with materialThe combined organic phases were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cccb71ca9e2b403db04f246fa54e2586
Source dataset
uspto-grants-2012_03
Patent number
US08143261B2

Reaction notes

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