2-Methylbenzenesulfonamide → HCID 14882520, compound

HRID 330157Notes

Reaction equation

HRID 330157 reaction equation
[CH2:1]([NH:4][C:5](/[CH:7]=[CH:8]/[C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][N:15]2[CH2:18][C:19]2[CH:27]=[CH:26][C:22]([C:23]([OH:25])=O)=[CH:21][C:20]=2[O:28][CH3:29])=[CH:11][CH:10]=1)=[O:6])[CH2:2][CH3:3].Cl.CN(C)CCCN=C=NCC.[CH3:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[S:49]([NH2:52])(=[O:51])=[O:50].N=C=N>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([NH:4][C:5](/[CH:7]=[CH:8]/[C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][N:15]2[CH2:18][C:19]2[CH:27]=[CH:26][C:22]([C:23]([NH:52][S:49]([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=3[CH3:42])(=[O:50])=[O:51])=[O:25])=[CH:21][C:20]=2[O:28][CH3:29])=[CH:11][CH:10]=1)=[O:6])[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 69242-MethylbenzenesulfonamideHCID 160435CarbodiimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14882511HCID 14882511, compound

Product 1

HCID 14882520HCID 14882520, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of E-4-[6-[2-(propylcarbamoyl)vinyl]indol-1-ylmethyl]-3-methoxybenzoic acid (0.76 g), 4-dimethylaminopyridine (0.26 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.41 g), and 2-methylbenzenesulfonamide (0.36 g) in methylene chloride (20 ml) was stirred under an atmosphere of nitrogen for 18 hr. Further quantities of 4-dimethylaminopyridine (0.026 g), the carbodiimide (0.041 g), and the sulfonamide (0.036 g) were added, and stirring was continued for a further 5 hr. The mixture was diluted with methylene chloride (40 ml); washed with 1M hydrochloric acid, water (twice) and brine; dried (MgSO4); and evaporated to give a foam. Crystallization from hot acetonitrile provided the title compound (0.75 g, 71%) as an off-white solid; mp 240°-242°.

Workup

  1. stirringstirring
  2. waitwas continued for a further 5 hr
  3. washwashed with 1M hydrochloric acid, water (twice) and brine
  4. dry with materialdried (MgSO4)
  5. customand evaporated
  6. customto give a foam
  7. customCrystallization from hot acetonitrile

Sources & evidence

ORD record
ord-be9a5c9b8f71428496a293e60c7ccaf2
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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