Methanesulfonyl chloride → HCID 22621018, compound

HRID 610766Notes

Reaction equation

HRID 610766 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([Cl:11])[C:5]=1[NH2:12].[CH3:14][S:15](Cl)(=[O:17])=[O:16]>O>[Cl:11][C:6]1[C:5]([NH:12][S:15]([CH3:14])(=[O:17])=[O:16])=[C:4]([CH:9]=[CH:8][C:7]=1[Cl:10])[C:3]([O:2][CH3:1])=[O:13]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chloride2×HCID 22621099Benzoic acid, 2-amino-3,4-dichloro-, methyl ester

Product 1

HCID 22621018HCID 22621018, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl-2-amino-3,4-dichlorobenzoate (2.2 g) and methanesulphonyl chloride (2.86 g) was stirred at 100° C. for 4 hours. A further quantity of methanesulphonyl chloride (2.86 g) was added and the mixture was stirred at 100° C. overnight. The mixture was poured into water then extracted with ethyl acetate. The combined organic extracts were washed with water, dried (magnesium sulphate) and evaporated to yield a brown oil which was crystallised from cyclohexane/ethyl acetate to yield methyl 3,4-dichloro-2-(methylsulphonylamino)benzoate as light brown crystals (1.4 g), m.p. 100-102° C.

Workup

  1. stirringthe mixture was stirred at 100° C. overnight
  2. extractionthen extracted with ethyl acetate
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried (magnesium sulphate)
  5. customevaporated
  6. customto yield a brown oil which
  7. customwas crystallised from cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-bedcd812ac9840d7873a35a2f45619ec
Source dataset
uspto-grants-1999_12
Patent number
US05998653

Reaction notes

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