Dimethylacetamide → HCID 57901797, compound

HRID 1851568Notes

Reaction equation

HRID 1851568 reaction equation
Cl[CH2:2][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.[CH3:24][NH:25][C:26]([NH2:28])=[S:27].CN(C)C(=O)C>C(OCC)(=O)C>[CH3:23][N:14]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[NH:6][C:5]([C:3]1[N:28]=[C:26]([NH:25][CH3:24])[S:27][CH:2]=1)=[CH:13]2)[S:15]([C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 2723704MethylthioureaHCID 57901842HCID 57901842, compound

Product 1

HCID 57901797HCID 57901797, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixed solution of N-[2-(2-chloroacetyl)-1H-indol-7-yl]-N-methylthiophene-2-sulfonamide (100 mg), N-methylthiourea (30 mg) and N,N-dimethylacetamide (6 ml) was stirred at 60° C. for 5 hr. The reaction solution was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:3-1:1), and the obtained oil was crystallized from ethyl acetate-hexane to give the title compound (84 mg, yield 77%) as pale-yellow prism crystals. melting point 162-163° C. MS:405 (MH+).

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customthe obtained oil was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-919d44f6a98f448db12c129dcf39d3e8
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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