Dimethylformamide → HCID 57476062, compound

HRID 1851422Notes

Reaction equation

HRID 1851422 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 at room temperature overnight. The reaction mixture was diluted with ethyl acetate and saturated brine and washed with saturated brine. The organic layer was 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. washwashed with saturated brine
  2. dry with materialThe organic layer was dried 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-afd3800d18fb4fa699f6e058784e06c2
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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