Water → HCID 10198779, compound

HRID 1057437Notes

Reaction equation

HRID 1057437 reaction equation
Cl[CH2:2][CH2:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C(N(C(C)C)CC)(C)C.O>CS(C)=O.C(OCC)(=O)C>[N:14]1([CH2:2][CH2:3][C:4]2[CH:5]=[C:6]3[C:10](=[CH:11][CH:12]=2)[NH:9][C:8](=[O:13])[CH2:7]3)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 145813925-(2-Chloroethyl)Oxindole

Product 1

HCID 10198779HCID 10198779, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Chloroethyl-2-oxindole (2.3 g), 1.2 mL of morpholine and 1.2 mL of diisopropylethylamine were heated overnight at 100° C. in 10 mL of dimethylsulfoxide. The mixture ws cooled, poured into water and extacted with ethyl acetate. The organic layer was washed with brine, dried and evaporated. The residue was chromatographed on silica gel in 5% methanol in chloroform to give 0.9 g (31%) of the title compound as a white solid.

Workup

  1. temperatureThe mixture ws cooled
  2. washThe organic layer was washed with brine
  3. customdried
  4. customevaporated
  5. customThe residue was chromatographed on silica gel in 5% methanol in chloroform

Sources & evidence

ORD record
ord-a61038e9b18241fb89b5c4d942bf4e2c
Source dataset
uspto-grants-2003_02
Patent number
US06514981B1

Reaction notes

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