4-Nitrobenzenesulfonamide → N-(4-Nitrophenylsulphonyl)-4-[3-(2-benzyloxyphenyl),propyl]benzamide

HRID 2395034

Reaction equation

HRID 2395034 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][CH2:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:27]([C:30]1[CH:35]=[CH:34][C:33]([S:36]([NH2:39])(=[O:38])=[O:37])=[CH:32][CH:31]=1)([O-:29])=[O:28].Cl.CN(C)CCCN=C=NCC>CN(C1C=CN=CC=1)C.CCOC(C)=O>[N+:27]([C:30]1[CH:31]=[CH:32][C:33]([S:36]([NH:39][C:22](=[O:23])[C:21]2[CH:25]=[CH:26][C:18]([CH2:17][CH2:16][CH2:15][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:19][CH:20]=2)(=[O:37])=[O:38])=[CH:34][CH:35]=1)([O-:29])=[O:28]

Participants

6

Reactant 3

HCID 227844-NitrobenzenesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 189737644-(3-(2-Benzyloxyphenyl)propyl]benzoic acid

Product 1

HCID 18973867N-(4-Nitrophenylsulphonyl)-4-[3-(2-benzyloxyphenyl),propyl]benzamideYield 68.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-[3-(2-benzyloxyphenyl)propyl)benzoic acid 0.2 g), 4-nitrobenzenesulphonamide (0.12 g), DMAP (0.15 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.12 g) was stirred for 65 hours. The mixture was diluted with EtOAc, washed with water and brine, dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel, eluting with ethyl acetate, to give the title compound (0.21 g) mpt. 112°-113° C.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-88281c07bdd14ad4bf75ece76666dd74
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Linked notes

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