2-Methylbenzenesulfonamide → HCID 14882549, compound

HRID 330164Notes

Reaction equation

HRID 330164 reaction equation
[O:1]=[C:2]([N:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1)/[CH:3]=[CH:4]/[C:5]1[C:13]2[C:8](=[CH:9][C:10](/[CH:14]=[CH:15]/[C:16]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:17])=[CH:11][CH:12]=2)[N:7]([CH2:23][C:24]2[CH:32]=[CH:31][C:27]([C:28]([OH:30])=O)=[CH:26][C:25]=2[O:33][CH3:34])[CH:6]=1.Cl.CN(C)CCCN=C=NCC.[CH3:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[S:59]([NH2:62])(=[O:61])=[O:60]>CN(C)C1C=CN=CC=1.CN(C)C=O.C(Cl)Cl.CO>[O:1]=[C:2]([N:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1)/[CH:3]=[CH:4]/[C:5]1[C:13]2[C:8](=[CH:9][C:10](/[CH:14]=[CH:15]/[C:16]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:17])=[CH:11][CH:12]=2)[N:7]([CH2:23][C:24]2[CH:32]=[CH:31][C:27]([C:28]([NH:62][S:59]([C:54]3[CH:55]=[CH:56][CH:57]=[CH:58][C:53]=3[CH3:52])(=[O:60])=[O:61])=[O:30])=[CH:26][C:25]=2[O:33][CH3:34])[CH:6]=1

Participants

8

Reactant 3

HCID 69242-MethylbenzenesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14882548HCID 14882548, compound

Product 1

HCID 14882549HCID 14882549, compoundYield 84.4%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of E,E-4-[3,6-Di(3-oxo-3-pyrrolidino-1-propenyl)indol-1-ylmethyl]-3-methoxybenzoic acid (0.45 g), 4-dimethylaminopyridine (0.13 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.21 g) and 2-methylbenzenesulfonamide (0.19 g), in N,N-dimethylformamide (10 ml) and methylene chloride (25 ml), was stirred for 48 hr. The methylene chloride was evaporated and the remaining solution added slowly to rapidly-stirred 2M hydrochloric acid (100 ml), the precipitate isolated by filtration and washed with water. The solid obtained was heated to reflux in methanol (50 ml), cooled, and the product isolated by filtration to give the title compound (0.49 g, 84%) as a yellow powder, mp 297°-299°.

Workup

  1. customThe methylene chloride was evaporated
  2. additionthe remaining solution added slowly
  3. customthe precipitate isolated by filtration
  4. washwashed with water
  5. customThe solid obtained
  6. temperaturewas heated
  7. temperaturecooled
  8. customthe product isolated by filtration

Sources & evidence

ORD record
ord-0c345997e06a435b84cf4c6c6bb55972
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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