Water → N-(2-Indanyl)-4-{N-methyl-N-[(E)-3-(3,4-diacetoxyphenyl)-2-propenoyl]amino}benzenesulfonamide

HRID 1377025Notes

Reaction equation

HRID 1377025 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][C:15]=1[O:16][C:17](=[O:19])[CH3:18])[CH:8]=[CH:9][C:10](Cl)=[O:11])(=[O:3])[CH3:2].[CH2:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH:21]1[NH:29][S:30]([C:33]1[CH:38]=[CH:37][C:36]([NH:39][CH3:40])=[CH:35][CH:34]=1)(=[O:32])=[O:31].O>ClCCl.N1C=CC=CC=1>[CH2:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:20][CH:21]1[NH:29][S:30]([C:33]1[CH:34]=[CH:35][C:36]([N:39]([CH3:40])[C:10](=[O:11])/[CH:9]=[CH:8]/[C:7]2[CH:13]=[CH:14][C:15]([O:16][C:17](=[O:19])[CH3:18])=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:6]=2)=[CH:37][CH:38]=1)(=[O:32])=[O:31]

Participants

6

Reactant 3

HCID 962WaterHCID 15049674N-(2-indanyl)-4-(methylamino)benzenesulfonamideHCID 545330334-(3-Chloro-3-oxoprop-1-en-1-yl)-1,2-phenylene diacetate

Product 1

HCID 15049696N-(2-Indanyl)-4-{N-methyl-N-[(E)-3-(3,4-diacetoxyphenyl)-2-propenoyl]amino}benzenesulfonamideYield 100%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3,4-diacetoxycinnamoyl chloride (5.61 g, 19.9 mmol) in dichloromethane (50 ml) was dropped into a solution of the N-(2-indanyl)-4-(methylamino)benzenesulfonamide (5.00 g, 16.6 mmol) prepared in Preparative Example 14 in pyridine (50 ml) at 0° C. The obtained mixture was stirred at room temperature for 2 hours, followed by the addition of water. The obtained mixture was extracted with ethyl acetate. The organic layer was washed with 1N aqueous hydrochloric acid and a saturated aqueous solution of common salt, dried over magnesium sulfate, and concentrated to give a solid residue. This residue was recrystallized from ethyl acetate/ether/isopropyl ether to give the title compound as a white crystal (8.90 g, 100%). m.p. (°C.): 152~153 (iso-Pr2O)

Workup

  1. extractionThe obtained mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 1N aqueous hydrochloric acid
  3. dry with materiala saturated aqueous solution of common salt, dried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give a solid residue
  6. customThis residue was recrystallized from ethyl acetate/ether/isopropyl ether

Sources & evidence

ORD record
ord-e68f7c044cd04c55a6b947083abe1d91
Source dataset
uspto-grants-1997_09
Patent number
US05663414

Reaction notes

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