Methanesulfonyl chloride → HCID 22621018, compound

HRID 430433Notes

Reaction equation

HRID 430433 reaction equation
[NH2:1][C:2]1[C:11]([Cl:12])=[C:10]([Cl:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:14][S:15](Cl)(=[O:17])=[O:16]>O>[Cl:12][C:11]1[C:2]([NH:1][S:15]([CH3:14])(=[O:17])=[O:16])=[C:3]([CH:8]=[CH:9][C:10]=1[Cl:13])[C:4]([O:6][CH3:7])=[O:5]

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-5d487229091447dd97873cde4e9a9d09
Source dataset
uspto-grants-2001_11
Patent number
US06323155B1

Reaction notes

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