1,2-Dichloroethane → 4-{[4-(3-Phenyl-indole-1-sulfonyl)-benzoylamino]-methyl}-benzoic acid

HRID 737023Notes

Reaction equation

HRID 737023 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([S:16]([C:19]3[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ONC(=O)CCC(N)=O.C(Cl)CCl.[NH2:41][CH2:42][C:43]1[CH:51]=[CH:50][C:46]([C:47]([OH:49])=[O:48])=[CH:45][CH:44]=1>ClCCl>[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([S:16]([C:19]3[CH:20]=[CH:21][C:22]([C:23]([NH:41][CH2:42][C:43]4[CH:44]=[CH:45][C:46]([C:47]([OH:49])=[O:48])=[CH:50][CH:51]=4)=[O:24])=[CH:26][CH:27]=3)(=[O:17])=[O:18])[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 655264-(Aminomethyl)Benzoic AcidHCID 18381240N-hydroxysuccinamideHCID 589751414-(3-Phenyl-indole-1-sulfonyl)-benzoic acid2×

Product 1

HCID 589751044-{[4-(3-Phenyl-indole-1-sulfonyl)-benzoylamino]-methyl}-benzoic acidYield 48.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Combine 4-(3-Phenyl-indole-1-sulfonyl)-benzoic acid (1.324 mmole) with N-hydroxy-succinamide (NHS− 1.457 mmoles), and EDC (1.324 mmoles) and stir in 20 ml dichloromethane for 15 hr. Condense the reaction to produce a solid. Isolate 0.613 g (yield=97.6%). React 1.05 mmole of residue with 4-aminomethyl-benzoic acid (1.05 mmole) in 3 ml dichloromethane for 15 hrs. Dilute reaction mixture and wash with 1 N HCl. Treat dichloromethane with MgSO4 and concentrate. Isolate a mixture of 4-(3-Phenyl-indole-1-sulfonyl)-benzoic acid and the title compound 0.258 g (48%): MS ES+ 5.10-77 MS ES− 509.21.

Workup

  1. customCondense
  2. customthe reaction
  3. customto produce a solid
  4. customIsolate 0.613 g (yield=97.6%)
  5. additionDilute
  6. customreaction mixture
  7. washwash with 1 N HCl
  8. concentrationTreat dichloromethane with MgSO4 and concentrate
  9. customIsolate

Sources & evidence

ORD record
ord-5ea9d14384f44cf484c5ff9e246e5483
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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