Water → HCID 18976149, compound

HRID 2393589Notes

Reaction equation

HRID 2393589 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][CH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]1=[O:19].[Cl:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1[Cl:30])[C:24](Cl)=[O:25].O>C(Cl)Cl>[Cl:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1[Cl:30])[C:24]([NH:9][CH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]1=[O:19])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 3552893-Amino-1,3-dihydro-2H-indol-2-one hydrochloride

Product 1

HCID 18976149HCID 18976149, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under argon atmosphere and ice cooling, a solution of 16.5 g of triethylamine in 50 ml of methylene chloride was added dropwise to a stirred mixture of 15.05 g of 3-amino-2,3-dihydro-1H-indol-2-one hydrochloride and 17.20 g of 3,4-dichlorobenzoyl chloride suspended in 300 ml of methylene chloride. The mixture was stirred at room temperature for 30 minutes. The reaction mixture was treated with 100 ml of water, and the whole was stirred for additional 2 hours. The resulting precipitates were collected by filtration, washed and then recrystallized from dimethylformamide-water to afford 22.9 g of 3,4-dichloro-N-(2,3-dihydro-2-oxo-1H-indol-3-yl)benzamide as colorless needle crystals. Melting point: 283° to 285° C. (decomposed), IR (Nujol) (cm-1) : 3280, 3160, 3100, 1710, 1690, 1635, MS (m/z): 322 & 320 (M+), 147 (base).

Workup

  1. stirringthe whole was stirred for additional 2 hours
  2. customThe resulting precipitates
  3. filtrationwere collected by filtration
  4. washwashed
  5. customrecrystallized from dimethylformamide-water

Sources & evidence

ORD record
ord-ad60bba2759845ddba10fb2219156af1
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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