HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Benzo[b]thiophene-2-sulfonic acid (2-aminophenyl)amide → Benzo[b]thiophene-2-sulfonic acid [2-(5-ethenesulfonyl-2-methoxybenzenesulfonylamino)phenyl] amide

HRID 730223
Notes
Print preview

Reaction equation

HRID 730223 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([C:12]1[S:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[CH:13]=1)(=[O:11])=[O:10].[CH:21]([S:23]([C:26]1[CH:27]=[CH:28][C:29]([O:36][CH3:37])=[C:30]([S:32](Cl)(=[O:34])=[O:33])[CH:31]=1)(=[O:25])=[O:24])=[CH2:22]>C(Cl)Cl.N1C=CC=CC=1>[CH:21]([S:23]([C:26]1[CH:27]=[CH:28][C:29]([O:36][CH3:37])=[C:30]([S:32]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[NH:8][S:9]([C:12]2[S:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[CH:13]=2)(=[O:11])=[O:10])(=[O:33])=[O:34])[CH:31]=1)(=[O:24])=[O:25])=[CH2:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 86240018Benzo[b]thiophene-2-sulfonic acid (2-aminophenyl)amideHCID 862400815-Ethenesulfonyl-2-methoxybenzenesulfonyl chloride

Product 1

HCID 86605045Benzo[b]thiophene-2-sulfonic acid [2-(5-ethenesulfonyl-2-methoxybenzenesulfonylamino)phenyl] amideYield 49.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent
HCID 6344
Dichloromethane
Solvent
2×

Procedure

To a solution of benzo[b]thiophene-2-sulfonic acid (2-aminophenyl)-amide (10 mmol, prepared as in Example 1) in DCM (20 mL) and pyridine (20 mL), 5-ethenesulfonyl-2-methoxybenzenesulfonyl chloride (11 mmol) was added at RT and the reaction mixture was then allowed to stir at RT overnight. The reaction mixture was then diluted with DCM (100 mL). The organic phase was washed with 10% aqueous HCl (100 mL), water (100 mL) and brine (100 mL). The organic phase was dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue obtained was purified by flash column chromatography eluting with DCM/EtOAc to obtain benzo[b]thiophene-2-sulfonic acid [2-(5-ethenesulfonyl-2-methoxybenzenesulfonylamino)phenyl] amide (2.8 g). LC: Tr 1.15 min; MS: 565.9 (M+1)+. 1H NMR (CDCl3, 400 MHz): δ 4.17 (s, 3H), 6.03 (d, 1H), 6.42 (d, 1H), 6.56 (dd, 1H), 6.81 (dd, 1H), 6.97 (t, 1H), 7.13 (t, 1H), 7.18 (d, 1H), 7.32 (d, 1H), 7.42-7.52 (m, 2H), 7.62 (s, 1H), 7.80 (d, 1H), 7.83 (d, 1H), 8.04 (dd, 1H), 8.19 (d, 1H) ppm.

Workup

  1. washThe organic phase was washed with 10% aqueous HCl (100 mL), water (100 mL) and brine (100 mL)
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue obtained
  5. customwas purified by flash column chromatography
  6. washeluting with DCM/EtOAc

Sources & evidence

ORD record
ord-128c2b2c43974cedb7804b522ed90e81
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07582673B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes