3-Chloropropanesulphonyl chloride → Methyl 2-(4-(3-chloropropylsulfonamido)phenyl)-2-methoxyacetate

HRID 2359183Notes

Reaction equation

HRID 2359183 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:13][CH3:14])[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[Cl:15][CH2:16][CH2:17][CH2:18][S:19](Cl)(=[O:21])=[O:20]>N1C=CC=CC=1.O.Cl.[Cl-].[Na+].O>[Cl:15][CH2:16][CH2:17][CH2:18][S:19]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([O:13][CH3:14])[C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1)(=[O:21])=[O:20]

Participants

7

Reactant 2

HCID 154103-Chloropropanesulphonyl chlorideHCID 58431984Methyl 2-(4-aminophenyl)-2-methoxyacetate

Product 1

HCID 58432097Methyl 2-(4-(3-chloropropylsulfonamido)phenyl)-2-methoxyacetateYield 99.9%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 1049PyridineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of methyl 2-(4-aminophenyl)-2-methoxyacetate (0.6 g, 3.07 mmol) in anhydrous pyridine (6 mL) under argon was added 3-chloropropane-1-sulfonyl chloride (0.5 mL, 4.11 mmol) dropwise. The exothermic reaction was cooled briefly over a cold H2O bath. After stirring for 1 hr, the reaction was diluted with H2O, 1 M HCl and brine and extracted with EtOAc. The combined organics were washed with 1 M HCl, H2O and brine then dried over Na2SO4 and concentrated in vacuo to give methyl 2-(4-(3-chloropropylsulfonamido)phenyl)-2-methoxyacetate as an orange oil (1.03 g, quant. yield). The product was used without further purification.

Workup

  1. customThe exothermic reaction
  2. temperaturewas cooled briefly over a cold H2O bath
  3. extractionextracted with EtOAc
  4. washThe combined organics were washed with 1 M HCl, H2O and brine
  5. dry with materialthen dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cba21d40b9bb4e39b315148861fe1944
Source dataset
uspto-grants-2014_04
Patent number
US08685975B2

Reaction notes

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