Hydrochloric Acid → HCID 22621022, compound

HRID 1953123Notes

Reaction equation

HRID 1953123 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[NH2:12].C(N(CC)CC)C.Cl[C:21]([O:23][CH3:24])=[O:22].Cl>C1COCC1.O>[Cl:1][C:2]1[C:3]([NH:12][C:21]([O:23][CH3:24])=[O:22])=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 43395852-Amino-3,4-dichlorobenzoic acid

Product 1

HCID 22621022HCID 22621022, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

3,4-Dichloroanthranilic acid (61.8 g) was stirred in THF at -15° C., and triethylamine was added. Methyl chloroformate (36.9 g) was then added at -15° C. and the mixture stirred for 45 minutes. Water was then added, followed by concentrated hydrochloric acid solution until pH 1 was achieved, and the solution was stirred overnight. Excess water was added and the mixture was extracted with ethyl acetate. The extract was washed with water, dried (anhydrous magnesium sulphate) and the solvent evaporated. The resulting solid was recrystallized from a solution of toluene and cyclohexane to give 3,4-dichloro-2-(methoxycarbonylamino)benzoic acid (65.1 g) as a fawn solid, m.p. 155-156° C.

Workup

  1. stirringthe solution was stirred overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried (anhydrous magnesium sulphate)
  5. customthe solvent evaporated
  6. customThe resulting solid was recrystallized from a solution of toluene and cyclohexane

Sources & evidence

ORD record
ord-b7a6bc8c95094c8b98a79bea0483bb4d
Source dataset
uspto-grants-2000_09
Patent number
US06114538

Reaction notes

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