Hydrochloric Acid → HCID 53748185, compound

HRID 1462933Notes

Reaction equation

HRID 1462933 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][SH:3].[Cl-].[CH2:7]([O:9][C:10]1[CH:11]=[C:12]([N+]#N)[CH:13]=[CH:14][CH:15]=1)[CH3:8].C(OC1C=C(C=CC=1)N)C.Cl>O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:7]([O:9][C:10]1[CH:15]=[C:14]([CH:2]([SH:3])[C:1]([OH:5])=[O:4])[CH:13]=[CH:12][CH:11]=1)[CH3:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1133Thioglycolic AcidHCID 121203-EthoxyanilineHCID 12823314HCID 12823314, compound

Product 1

HCID 53748185HCID 53748185, compound

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent

Procedure

32.2 g of thioglycolic acid and 56.4 g of crystalline copper sulphate are stirred for 30 minutes in 250 ml of water. Then an aqueous solution of 3-ethoxyphenyldiazonium chloride, prepared according to Example 1(a) from 34.3 g of 3-ethoxyaniline, is allowed to run in at 25° C. in 20 minutes. After a further 40 minutes' stirring, 64 ml of 36% strength hydrochloric acid are added. The mixture is stirred for 1 hour at 40°-50° C., filtered hot with suction and washed with 5% strength hydrochloric acid. The moist filtered solid is dissolved in 500 ml of water with 30 g of sodium carbonate, and heated to boiling with 5 g of active charcoal for 15 minutes. It is filtered hot and the filtrate is added to 85 ml of 36% strength hydrochloric acid to precipitate the 3-ethoxyphenylthioglycolic acid. It is filtered off with suction, washed with a little water and dried. 40.4 g of 3-ethoxyphenylthioglycolic acid are obtained, which is 75.7% of theory. The acid is 99.5% pure with a melting point of 105°-107° C.

Workup

  1. stirringThe mixture is stirred for 1 hour at 40°-50° C.
  2. filtrationfiltered hot with suction
  3. washwashed with 5% strength hydrochloric acid
  4. filtrationThe moist filtered solid
  5. dissolutionis dissolved in 500 ml of water with 30 g of sodium carbonate
  6. temperatureheated
  7. waitto boiling with 5 g of active charcoal for 15 minutes
  8. filtrationIt is filtered hot
  9. additionthe filtrate is added to 85 ml of 36% strength hydrochloric acid
  10. customto precipitate the 3-ethoxyphenylthioglycolic acid
  11. filtrationIt is filtered off with suction
  12. washwashed with a little water
  13. customdried

Sources & evidence

ORD record
ord-2c3a4c7377a241a0a692b1fe2a4cf386
Source dataset
uspto-grants-1984_07
Patent number
US04461911

Reaction notes

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