Hydrochloric Acid → HCID 178526168, compound

HRID 2052399Notes

Reaction equation

HRID 2052399 reaction equation
NC(N)=[S:3].Cl[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1.[OH-].[Na+].Cl[CH2:20][C:21]([O-:23])=O.[Na+].Cl>O>[C:7]1([CH:6]=[CH:20][C:21]([OH:23])=[S:3])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 68451-ChloromethylnaphthaleneHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 23665759Sodium chloroacetate

Product 1

HCID 178526168HCID 178526168, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 15.2 g (0.2 mol) of thiourea in 100 ml of water is introduced into a 1 liter three-necked flask equipped with a magnetic stirrer, a condenser and a dropping funnel, and 35.3 g (0.2 mol) of α-chloromethylnaphthalene are added all at once, at 50°-60° C. The mixture is heated until it reaches the refluxing temperature and is kept at the boil for quarter of an hour. The thiouronium salt precipitates. The mixture is then cooled and a solution of 32 g of sodium hydroxide (0.8 mol) in 50 ml of water is then added dropwise at about 60° C. The resulting mixture is heated under reflux until the solution becomes limpid and is then cooled, and a solution of about 0.28 mol of sodium chloroacetate (obtained by neutralising 26.36 g of chloroacetic acid with 23.52 g of sodium bicarbonate in 200 ml of water) is (then) added dropwise at 60°-70° C. The whole is then heated under reflux for half an hour after which it is cooled and acidified in the cold by adding 3 N HCl, thus precipitating α-naphthylmethylene-thiacetic acid, which is filtered off. 44.5 g of product are collected (yield: 95%). Instantaneous melting point=102°-103° C.

Workup

  1. customequipped with a magnetic stirrer, a condenser and a dropping funnel
  2. temperatureThe mixture is heated until it
  3. waitis kept at the boil for quarter of an hour
  4. customThe thiouronium salt precipitates
  5. temperatureThe mixture is then cooled
  6. temperatureThe resulting mixture is heated
  7. temperatureunder reflux until the solution
  8. temperatureis then cooled
  9. additionadded dropwise at 60°-70° C
  10. temperatureThe whole is then heated
  11. temperatureunder reflux for half an hour after which it
  12. temperatureis cooled
  13. filtrationis filtered off
  14. custom44.5 g of product are collected (yield: 95%)

Sources & evidence

ORD record
ord-3e7f60c0e6fb4b68b58861dde217c8d8
Source dataset
uspto-grants-1980_01
Patent number
US04183951

Reaction notes

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