Hydrochloric Acid → HCID 23075416, compound

HRID 33601Notes

Reaction equation

HRID 33601 reaction equation
[NH2:1][C:2]1[C:3]([CH3:27])=[C:4]2[C:8](=[C:9]([NH:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[C:10]=1[CH3:11])[N:7]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:6][CH2:5]2.[Cl:28]S([N:32]=[C:33]=[O:34])(=O)=O.Cl.O>C(Cl)Cl>[ClH:28].[CH3:27][C:3]1[C:2]([NH:1][C:33]([NH2:32])=[O:34])=[C:10]([CH3:11])[C:9]([NH:12][C:13](=[O:18])[C:14]([CH3:16])([CH3:17])[CH3:15])=[C:8]2[C:4]=1[CH2:5][CH2:6][N:7]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 23075425N-(5-Amino-4,6-dimethyl-1-octylindolin-7-yl)-2,2-dimethylpropanamide

Product 1

HCID 23075416HCID 23075416, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(5-Amino-4,6-dimethyl-1-octylindolin-7-yl)-2,2-dimethylpropanamide (500 mg) was dissolved in methylene chloride (5.0 mL), and chlorosulfonyl isocyanate (0.14 mL) was added dropwise at −60° C. The mixture was stirred at the same temperature for 3 hr and 6M hydrochloric acid (0.45 mL) was added. The mixture was stirred at room temperature for 30 min. Water (50 mL) was added to the reaction solution and the mixture was extracted with chloroform (100 mL). The chloroform layer was washed with saturated brine and dried over sodium sulfate. Chloroform was evaporated under reduced pressure and the obtained crystalline residue was recrystallized from a mixture of chloroform-diisopropyl ether to give the title compound as crystals (407 mg).

Workup

  1. stirringThe mixture was stirred at room temperature for 30 min
  2. extractionthe mixture was extracted with chloroform (100 mL)
  3. washThe chloroform layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customChloroform was evaporated under reduced pressure
  6. customthe obtained crystalline residue was recrystallized from a mixture of chloroform-diisopropyl ether

Sources & evidence

ORD record
ord-97faa260617b47e7aceb3f11cb388ad3
Source dataset
uspto-grants-2008_09
Patent number
US07429612B2

Reaction notes

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