Dimethylformamide → HCID 57476062, compound

HRID 1960253Notes

Reaction equation

HRID 1960253 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-452fe8fffb1646fd8285a1d2d73f4112
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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