Dichloromethane → HCID 70024758, compound

HRID 1358462Notes

Reaction equation

HRID 1358462 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:23])[CH2:12][C:13]2[CH:18]=[C:17]([Br:19])[C:16]([O:20][CH3:21])=[C:15]([Br:22])[CH:14]=2)=[CH:4][C:3]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:32]1([S:38](Cl)(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(Cl)Cl>N1C=CC=CC=1>[C:32]1([S:38]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:23])[CH2:12][C:13]3[CH:18]=[C:17]([Br:19])[C:16]([O:20][CH3:21])=[C:15]([Br:22])[CH:14]=3)=[CH:4][C:3]=2[O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7369Benzenesulfonyl chlorideHCID 18184540HCID 18184540, compound

Product 1

HCID 70024758HCID 70024758, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-[2-(4-amino-3-benzyloxy-phenyl)-ethyl]-2-(3,5-dibromo-4-methoxy-phenyl)-acetamide (0.995 g, 0.00181 mol) and phenylsulfonyl chloride (0.484 g, 0.00274 mol) 40 mL of methylene chloride was added 5 mL of pyridine. The reaction mixture was stirred overnight at room temperature, washed with 1N HCl and 1N NaOH, dried over Na2SO4 and concentrated. A crystallization from ethyl acetate-hexanes gave an oil. It was solidified under standing. Yield 1.043 g (83%).

Workup

  1. washwashed with 1N HCl and 1N NaOH
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customA crystallization from ethyl acetate-hexanes
  5. customgave an oil

Sources & evidence

ORD record
ord-a8bb6d9eefca4466b9c99dd45f57c595
Source dataset
uspto-grants-2003_07
Patent number
US06596734B1

Reaction notes

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