Hydrogen Bromide → HCID 178490205, compound

HRID 1707021

Reaction equation

HRID 1707021 reaction equation
NC(N)=[S:3].Br.[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14]O)=[CH:12][CH:13]=1.[NH2+]=C(N)S.[OH-].[Na+].Cl[CH2:23][C:24]([OH:26])=O.Cl>O.C(Cl)Cl>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:23][C:24]([OH:26])=[S:3])=[CH:10][CH:9]=1

Participants

10

Reactant 7

HCID 260Hydrogen BromideHCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 77384-Methoxybenzyl alcoholHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 178512448HCID 178512448, compound

Product 1

HCID 178490205HCID 178490205, compoundYield 798.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 18.24 g (0.24 mol) of thiourea in 104 ml of 48% strength hydrobromic acid and 20 ml of water is introduced into a 1 liter three-necked flask equipped with a magnetic stirrer and a condenser. The mixture is heated at 60° C. and 27.6 g (0.2 mol) of p-methoxybenzyl alcohol are introduced. The temperature is raised to 95° C. and the mixture is then allowed to cool. Crystals of thiouronium salt appear; these are filtered off and suction-drained. The precipitate obtained above is introduced into a 500 ml three-necked flask together with 60 ml of NaOH. The mixture is heated to 70° C. and a solution of 15.6 g (0.0164 mol) of chloroacetic acid dissolved in 30 ml of water is added dropwise. The whole is then heated under reflux for half an hour, after which it is cooled. The mixture is acidified with 3 N HCl, the oil obtained is taken up in methylene chloride and washed with a dilute sodium bicarbonate solution and (?the aqueous phase) is filtered over charcoal and again acidified with 3 N HCl to precipitate p-methoxybenzylthioacetic acid. 25.7 g (60% yield) of the said acid (melting point=60° C.) are collected.

Workup

  1. customequipped with a magnetic stirrer and a condenser
  2. temperatureThe temperature is raised to 95° C.
  3. temperatureto cool
  4. filtrationthese are filtered off
  5. customThe precipitate obtained
  6. temperatureThe mixture is heated to 70° C.
  7. additionis added dropwise
  8. temperatureThe whole is then heated
  9. temperatureunder reflux for half an hour
  10. temperatureafter which it is cooled
  11. customthe oil obtained
  12. washwashed with a dilute sodium bicarbonate solution
  13. filtration(?the aqueous phase) is filtered over charcoal
  14. customto precipitate p-methoxybenzylthioacetic acid

Sources & evidence

ORD record
ord-849b4b0e291d4d90bc34a1747d07ef50
Source dataset
uspto-grants-1980_06
Patent number
US04209523

Linked notes

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