Chlorosulfonic acid → HCID 18541183, compound

HRID 411610Notes

Reaction equation

HRID 411610 reaction equation
C(CNC(=O)COC1C=CC=CC=1)(=O)N.[C:16]([CH2:19][NH:20][C:21](=[O:34])[CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([Cl:33])(=[O:32])=[O:31])=[CH:26][CH:25]=1)(=[O:18])[NH2:17].ClS(O)(=O)=O>ClCCl>[C:16]([CH2:19][NH:20][C:21](=[O:34])[CH2:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([S:30]([Cl:33])(=[O:31])=[O:32])=[CH:28][CH:29]=1)(=[O:18])[NH2:17]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 18541196HCID 18541196, compound

Product 1

HCID 18541183HCID 18541183, compoundYield 224.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Preparation of N-(carbamoylmethyl)-2-[4-(chlorosulfonyl)phenoxy]acetamide N-(carbamoylmethyl)-2-(phenoxy)acetamide (2.08 g) was resuspended in 30 ml of dichloromethane and chlorosulfonic acid (6 ml) was slowly added with cooling. The reaction mixture was stirred at room temperature for 2 hr. Two layers separated after standing for 10 min without stirring. Upper layer was decanted. Lower layer was poured to chopped ice (60 g) with good mixing to give white solid, which was collected by filtration and washed with ice-cold water. The solid was dried in vacuo to give 2.78 g of N-(carbamoylmethyl)-2-[4-(chlorosulfonyl)phenoxy]acetamide.

Workup

  1. temperaturewith cooling
  2. customTwo layers separated
  3. waitafter standing for 10 min
  4. stirringwithout stirring
  5. customUpper layer was decanted
  6. additionLower layer was poured to chopped ice (60 g)
  7. additionwith good mixing
  8. customto give white solid, which
  9. filtrationwas collected by filtration
  10. washwashed with ice-cold water
  11. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-dac1f3646152465fb9875da73cc7ce4d
Source dataset
uspto-grants-2003_05
Patent number
US06559167B1

Reaction notes

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