Dimethylformamide → HCID 57476062, compound

HRID 2238858Notes

Reaction equation

HRID 2238858 reaction equation
[CH2:1]([N:3]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][C:18]([C:21]1[S:22][C:23]([CH2:26]O)=[CH:24][N:25]=1)=[CH:17]2)[S:4]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)(=[O:6])=[O:5])[CH3:2].CN(C)C=O.O1CCCC1.S(Cl)([Cl:40])=O>C(OCC)(=O)C.[Cl-].[Na+].O>[Cl:40][CH2:26][C:23]1[S:22][C:21]([C:18]2[NH:19][C:20]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][C:12]=3[N:3]([CH2:1][CH3:2])[S:4]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)(=[O:6])=[O:5])=[N:25][CH:24]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 57475966HCID 57475966, compound

Product 1

HCID 57476062HCID 57476062, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of N-ethyl-N-{2-[5-(hydroxymethyl)-1,3-thiazol-2-yl]-1H-indol-7-yl}thiophene-2-sulfonamide (3.43 g), N,N-dimethylformamide (0.05 ml) and tetrahydrofuran (50 ml) was added thionyl chloride (1.56 g), and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate and saturated brine, and the organic layer was washed with saturated brine, and dried over magnesium sulfate, and filtrated. The filtrate was concentrated, and the obtained solid was washed with ether-hexane (1:1) to give the title compound (3.27 g, yield 91%) as a pale-yellow solid.

Workup

  1. washthe organic layer was washed with saturated brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltrated
  4. concentrationThe filtrate was concentrated
  5. washthe obtained solid was washed with ether-hexane (1:1)

Sources & evidence

ORD record
ord-0ac76f3d30ac4207890809dab8007a03
Source dataset
uspto-grants-2010_05
Patent number
US07718798B2

Reaction notes

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