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

HRID 1629839Notes

Reaction equation

HRID 1629839 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-28acd9d26007416288f95e8329d8ad61
Source dataset
uspto-grants-2014_07
Patent number
US08791103B2

Reaction notes

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