Hydrochloric Acid → 3-Amino-2-methyl-4-methylsulfanylbenzoic acid

HRID 1263400Notes

Reaction equation

HRID 1263400 reaction equation
N[C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]([O:13]C)=[O:12])=[C:7]([CH3:15])[C:5]=2[N:6]=1.[OH-].[Na+].S(OC)(OC)(=O)=O.Cl>O.C(O)CO.C1(C)C=CC=CC=1>[NH2:6][C:5]1[C:7]([CH3:15])=[C:8]([CH:9]=[CH:10][C:4]=1[S:3][CH3:2])[C:11]([OH:13])=[O:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 22390084Methyl 2-amino-4-methylbenzo[d]thiazole-5-carboxylate

Product 1

HCID 186160433-Amino-2-methyl-4-methylsulfanylbenzoic acid

Reagents, catalysts & solvents 3

HCID 174Ethylene GlycolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

10 g of methyl 2-amino-4-methylbenzothiazole-5-carboxylate (0.045 mol.) were dissolved in a mixture of 120 ml of water, 120 ml of ethylene glycol and 50 g of NaOH, and the mixture was stirred at 130° C. for 20 h. The mixture was then diluted with 50 g of ice, 3 drops of (n-Bu)4N+OH— solution were added and finally, at 20° C., 6.25 ml of dimethyl sulfate (0.05 mol) in 15 ml of toluene were added dropwise. After 30 min, the mixture was acidified with conc. HCl and the precipitate was filtered off with suction, washed with water and dried.

Workup

  1. additionwere added
  2. waitAfter 30 min
  3. filtrationthe precipitate was filtered off with suction
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-d4327a1cf2784c4cb42693e700677ae9
Source dataset
uspto-grants-2003_04
Patent number
US06541423B1

Reaction notes

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