Hydrochloric Acid → HCID 178427264, compound

HRID 1606621Notes

Reaction equation

HRID 1606621 reaction equation
[ClH:1].[NH2:2][C:3]1[CH:4]=[C:5]([CH:9]=C(S)[C:11]=1Cl)[C:6](O)=O.[OH-:14].[Na+].[S:16](OC)(OC)(=O)=O.Cl.[CH2:24](O)[CH3:25]>>[NH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:24]([CH3:25])[C:11]=1[Cl:1])[C:6]([OH:14])=[S:16]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6497Dimethyl SulfateHCID 14798Sodium Hydroxide2×HCID 68136852HCID 68136852, compound

Product 1

HCID 178427264HCID 178427264, compound

Procedure

A solution of 3-amino-4-chloro-5-mercaptobenzoic acid hydrochloride (23 g.; 0.096 mole) in 50% aqueous ethanol (350 ml.) is made basic with 10N sodium hydroxide to pH = 9, and refluxed while dimethyl sulfate (14.2 ml.) is added dropwise during a one-hour period. Heating is continued for three hours and 10N sodium hydroxide is added in small portions to maintain pH 9. The reaction is cooled and acidified with hydrochloric acid to give 18 g. of 3-amino-4-chloro-5-methylthiobenzoic acid (87%) which melts at 225° C. after recrystallization from ethanol.

Workup

  1. additionis added dropwise during a one-hour period
  2. temperatureHeating
  3. temperatureto maintain pH 9
  4. temperatureThe reaction is cooled
  5. customto give 18 g
  6. customof 3-amino-4-chloro-5-methylthiobenzoic acid (87%) which melts at 225° C. after recrystallization from ethanol

Sources & evidence

ORD record
ord-a815e04caf6b4d9f8e7f522cfb717fdf
Source dataset
uspto-grants-1976_04
Patent number
US03953476

Reaction notes

Loading…