Water → HCID 57901836, compound

HRID 1851545Notes

Reaction equation

HRID 1851545 reaction equation
[NH:1]([C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][C:8]=2[N:14]([CH3:23])[S:15]([C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)(=[O:17])=[O:16])=[O:4])[NH2:2].Cl[C:25](=[O:32])[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].O>CN(C)C(=O)C>[CH3:23][N:14]([S:15]([C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)(=[O:17])=[O:16])[C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[NH:6][C:5]([C:3]([NH:1][NH:2][C:25](=[O:32])[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:4])=[CH:13]2

Participants

5

Reactant 3

HCID 962WaterHCID 118931Ethyl 3-chloro-3-oxopropionateHCID 57901684HCID 57901684, compound

Product 1

HCID 57901836HCID 57901836, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of N-[2-(hydrazinocarbonyl)-1H-indol-7-yl]-N-methylthiophene-2-sulfonamide (0.88 g) in N,N-dimethylacetamide (16 mL) was added ethyl 3-chloro-3-oxopropanoate (0.35 mL) at 0° C., and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. Diethyl ether was added to the obtained oil, and the resulting crystals were filtrated, washed with diethyl ether, and dried to give the title compound (0.96 g, yield 84%) as colorless crystals. melting point 119-121° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. additionDiethyl ether was added to the obtained oil
  6. filtrationthe resulting crystals were filtrated
  7. washwashed with diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-6cd913c7333d4434867e2dd63b7663ee
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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