Hydrochloric Acid → HCID 178436709, compound

HRID 635266Notes

Reaction equation

HRID 635266 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([NH2:12])[C:9](S)=[CH:8][C:4]=1[C:5]([OH:7])=O.[Na].C(O[S:18]([O-])(=O)=O)C.Cl.CCO[CH2:26][CH3:27]>O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([NH2:12])[C:9]([CH2:26][CH3:27])=[CH:8][C:4]=1[C:5]([OH:7])=[S:18]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 34353994-Amino-2-methoxy-5-sulfanylbenzoic acidHCID 3804841Ethyl sulfate anionHCID 5360545Sodium2×

Product 1

HCID 178436709HCID 178436709, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

159 g of 2-methoxy-4-amino-5-mercaptobenzoic acid, 355 cm3 of water and 160 cm3 of 30% sodium hydroxyde solution are placed in a flask fitted with a condenser. The mixture is heated until the solid dissolves, then 123 g of ethylsulfate is added. The mixture is heated to reflux, treated with 10 cm3 of 30% sodium hydroxyde solution, then heated to reflux for 1 hour. After cooling, 800 cm3 of water is added and the solution is filtered. The precipitate obtained by adding 100 cm3 of concentrated hydrochloric acid in the presence of ether is drained, washed with water and dried. 162 g of 2-methoxy-4-amino-5-ethylthio benzoic acid is obtained (yield=88%).

Workup

  1. customfitted with a condenser
  2. temperatureThe mixture is heated until the solid
  3. dissolutiondissolves
  4. temperatureThe mixture is heated
  5. temperatureto reflux
  6. temperatureheated
  7. temperatureto reflux for 1 hour
  8. temperatureAfter cooling
  9. filtrationthe solution is filtered
  10. customThe precipitate obtained
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-e004ecc170f2474cbd6008843b8206aa
Source dataset
uspto-grants-2001_02
Patent number
US06187807B1

Reaction notes

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