4-Toluenesulfonyl chloride → HCID 71075774, compound

HRID 2170614Notes

Reaction equation

HRID 2170614 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[C:12]1([CH:18]([NH:21][C:22]([C:24]2[CH:25]=[C:26]3[C:30](=[CH:31][CH:32]=2)[NH:29][CH:28]=[CH:27]3)=[O:23])[CH2:19][CH3:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[K+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[C:12]1([CH:18]([NH:21][C:22]([C:24]2[CH:25]=[C:26]3[C:30](=[CH:31][CH:32]=2)[N:29]([S:1]([C:4]2[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=2)(=[O:3])=[O:2])[CH:28]=[CH:27]3)=[O:23])[CH2:19][CH3:20])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 63717133HCID 63717133, compound

Product 1

HCID 71075774HCID 71075774, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Tosyl chloride (1.1 equiv), benzyltriethylammonium chloride (0.5 equiv) was added to a solution of N-(1-phenylpropyl)-1H-indole-5-carboxamide in CH2Cl2, KOH (1.3 equiv) at room temperature. After the reaction was completed, the solvent was evaporated and the residual was purified by silica gel column chromatography to get the product. LC-MS 433 (M+H).

Workup

  1. customthe solvent was evaporated
  2. customthe residual was purified by silica gel column chromatography
  3. customto get the product

Sources & evidence

ORD record
ord-52e6ddfcfaa24178bbea905dfeb90a64
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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