Water → Methyl 4-(3-chloro-propyl-sulphonyl-amino)-3-methyl-benzoate

HRID 2094269Notes

Reaction equation

HRID 2094269 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12].[Cl:13][CH2:14][CH2:15][CH2:16][S:17](Cl)(=[O:19])=[O:18].O.C(OCC)(=O)C>N1C=CC=CC=1>[Cl:13][CH2:14][CH2:15][CH2:16][S:17]([NH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12])(=[O:19])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 154103-Chloropropanesulphonyl chlorideHCID 2736799Methyl 4-amino-3-methylbenzoate

Product 1

HCID 43654282Methyl 4-(3-chloro-propyl-sulphonyl-amino)-3-methyl-benzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

100 mg (0.61 mmol) methyl 4-amino-3-methyl-benzoate dissolved in 3 ml of pyridine are combined with 82 μl (0.67 mmol) 3-chloropropanesulphonic acid chloride and stirred for 16 hours at ambient temperature. The reaction solution is combined with water and ethyl acetate and then the aqueous phase is again extracted with ethyl acetate. The combined organic phases are dried over sodium sulphate and evaporated down i. vac. The residue is further reacted without any more purification.

Workup

  1. extractionthe aqueous phase is again extracted with ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. customevaporated down i
  4. customThe residue is further reacted without any more purification

Sources & evidence

ORD record
ord-acf9cc62eec942c88c0f6bf3e0426e6a
Source dataset
uspto-grants-2013_05
Patent number
US08445525B2

Reaction notes

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