Hydrochloric Acid → HCID 178526168, compound

HRID 2285934Notes

Reaction equation

HRID 2285934 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, compound

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-chloromethyl-naphthalene are added, all at once, at 50°-60° C. The reaction mixture is heated to the reflux temperature and boiling is maintained for a quarter of an hour. The thiouronium salt precipitates. Thereafter the mixture is cooled and a solution of 32 g of sodium hydroxide (0.8 mol) in 50 ml of water is added dropwise at about 60° C. The resulting mixture is heated under reflux until the solution becomes limpid, and is cooled and a solution of about 0.28 mol of sodium chloroacetate (obtained by neutralising 26.36 g of chloroacetic acid in 200 ml of water with 23.52 g of sodium bicarbonate) is added dropwise at 60°-70° C. The whole is then heated under reflux for half an hour, cooled and acidified cold by the addition of 3 N HCl. α-Naphthylmethylene-thioacetic acid thus precipitates, and is filtered off. 44.5 g of product are collected.

Workup

  1. customequipped with a magnetic stirrer, a condenser and a dropping funnel
  2. customat 50°-60° C
  3. temperatureThe reaction mixture is heated to the reflux temperature and boiling
  4. temperatureis maintained for a quarter of an hour
  5. customThe thiouronium salt precipitates
  6. temperatureThereafter the mixture is cooled
  7. temperatureThe resulting mixture is heated
  8. temperatureunder reflux until the solution
  9. temperatureis cooled
  10. temperatureThe whole is then heated
  11. temperatureunder reflux for half an hour
  12. temperaturecooled
  13. customα-Naphthylmethylene-thioacetic acid thus precipitates
  14. filtrationis filtered off
  15. custom44.5 g of product are collected

Sources & evidence

ORD record
ord-86a980c4159e45f1a550fc935272a397
Source dataset
uspto-grants-1982_04
Patent number
US04325964

Reaction notes

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