Chlorosulfonic acid → 4-(2-Amino-2-oxoethoxy)benzenesulfonyl chloride

HRID 1593261Notes

Reaction equation

HRID 1593261 reaction equation
[O:1]([CH2:8][C:9]([NH2:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:12][S:13](O)(=[O:15])=[O:14]>ClCCl>[Cl:12][S:13]([C:5]1[CH:6]=[CH:7][C:2]([O:1][CH2:8][C:9]([NH2:11])=[O:10])=[CH:3][CH:4]=1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 693142-Phenoxyacetamide

Product 1

HCID 116444964-(2-Amino-2-oxoethoxy)benzenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of phenoxyacetamide (50 g, 0.333 mol) in dichloromethane (500 mL) was added dropwise chlorosulfonic acid (174.7 g, 1.5 mol) at 0° C. at such a rate to maintain internal temperature between 0 to +5° C. (about 45 min). Some solid formed during this addition. The cooling bath was removed and the reaction mixture was stirred at room temperature overnight. The lower layer in the reaction mixture was added into a vigorously stirring mixture of water (500 mL) and crushed-ice (1500 g). The solid was collected, washed with water (750 mL), and pressed well with a rubber dam. The solid was suspended in acetone (100 mL), stirred for 30 min and collected. After drying, the title compound was isolated as a white solid, weighed 67.3 g (81%).

Workup

  1. temperatureto maintain internal temperature between 0 to +5° C. (about 45 min)
  2. customSome solid formed during this addition
  3. customThe cooling bath was removed
  4. additionThe lower layer in the reaction mixture was added into
  5. stirringa vigorously stirring
  6. additionmixture of water (500 mL)
  7. customcrushed-ice (1500 g)
  8. customThe solid was collected
  9. washwashed with water (750 mL)
  10. stirringstirred for 30 min
  11. customcollected
  12. customAfter drying

Sources & evidence

ORD record
ord-7d4ccac12fb14c0d9180fd3d2b43ff7a
Source dataset
uspto-grants-2007_11
Patent number
US07294716B2

Reaction notes

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