Hydrochloric Acid → 3-(2,4-Dichlorobenzyl)-5-(1-pentanesulfonylcarbamoyl)indole

HRID 1242145Notes

Reaction equation

HRID 1242145 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21])([OH:3])=O.C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1.[CH2:44]([S:49]([NH2:52])(=[O:51])=[O:50])[CH2:45][CH2:46][CH2:47][CH3:48].Cl>O.CN(C)C=O>[Cl:21][C:15]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=1[CH2:13][C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([C:1](=[O:3])[NH:52][S:49]([CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])(=[O:51])=[O:50])[CH:5]=2)[NH:9][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 98800965-Carboxy-3-(2,4-dichlorobenzyl)indoleHCID 109206961-PentanesulfonamideHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 219382503-(2,4-Dichlorobenzyl)-5-(1-pentanesulfonylcarbamoyl)indoleYield 42.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N,N′-Carbonyldiimidazole (0.282 g) is added to an N,N-dimethylformamide (4.3 ml) solution of 5-carboxy-3-(2,4-dichlorobenzyl)indole (0.429 g), and stirred at room temperature for 1 hour. Diazabicycloundecene (0.306 g) and 1-pentanesulfonamide (0.304 g) are added thereto, and stirred at 100° C. for 40 hours. The reaction mixture is cooled, and then made acidic with water and 1M HCl added thereto. Then, the gummy residue formed is collected. This is dissolved in ethyl acetate, washed with water, and died. The solvent is evaporated away, and the resulting residue is crystallized from ether. The crystal formed is collected and dried to obtain 3-(2,4-dichlorobenzyl)-5-(1-pentanesulfonylcarbamoyl)indole (88) (0.258 g).

Workup

  1. stirringstirred at 100° C. for 40 hours
  2. temperatureThe reaction mixture is cooled
  3. additionadded
  4. customThen, the gummy residue formed
  5. customis collected
  6. dissolutionThis is dissolved in ethyl acetate
  7. washwashed with water
  8. customThe solvent is evaporated away
  9. customthe resulting residue is crystallized from ether
  10. customThe crystal formed
  11. customis collected
  12. customdried

Sources & evidence

ORD record
ord-3c9c6c43e21e4a7e8e73426bfbdf0ef8
Source dataset
uspto-grants-2006_10
Patent number
US07115647B2

Reaction notes

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