P-Anisidine → HCID 69417668, compound

HRID 1593260Notes

Reaction equation

HRID 1593260 reaction equation
[C:1]([CH2:4][O:5][C:6]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][C:7]=1[O:8][CH2:9][C:10]([NH2:12])=[O:11])(=[O:3])[NH2:2].[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1>N1C=CC=CC=1>[C:10]([CH2:9][O:8][C:7]1[CH:13]=[C:14]([S:17]([NH:29][C:26]2[CH:27]=[CH:28][C:23]([O:22][CH3:21])=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH:15]=[CH:16][C:6]=1[O:5][CH2:4][C:1]([NH2:2])=[O:3])(=[O:11])[NH2:12]

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 185412373,4-Bis(carbamoylmethoxy)benzenesulfonyl chloride

Product 1

HCID 69417668HCID 69417668, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Solid 2-[2-(carbamoylmethoxy)-5-(chlorosulfonyl)phenoxy acetamide (Intermediate A85, 161.25 g, 0.5 mol) was added to a solution of p-anisidine (49.2 g, 0.4 mol) in pyridine (3.5 L) and stirred at room temperature overnight under argon. The reaction mixture was concentrated under reduce pressure. The residue was treated with 0.75 M hydrochloric acid (3 L) and the resulting solid was collected. The solid was washed with water (3×1 L), methanol (750 mL) and dried to give 99 g (60%) of the title compound, sulfonamide.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionThe residue was treated with 0.75 M hydrochloric acid (3 L)
  3. customthe resulting solid was collected
  4. washThe solid was washed with water (3×1 L), methanol (750 mL)
  5. customdried

Sources & evidence

ORD record
ord-d0c012a77a7741b1ae1f36928eedf060
Source dataset
uspto-grants-2007_11
Patent number
US07294716B2

Reaction notes

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