Tetrahydrofuran → HCID 59136056, compound

HRID 1851424Notes

Reaction equation

HRID 1851424 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][N:6]([C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:23]=1[NH:22][C:21]([C:24]1[S:25][C:26]([CH2:29]O)=[CH:27][N:28]=1)=[CH:20]2)[S:7]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)(=[O:9])=[O:8])[CH3:2].O1CCCC1.S(Cl)([Cl:38])=O>CN(C)C=O.C(OCC)(=O)C.[Cl-].[Na+].O>[Cl:38][CH2:29][C:26]1[S:25][C:24]([C:21]2[NH:22][C:23]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][C:15]=3[N:6]([CH2:5][CH2:4][O:3][CH2:1][CH3:2])[S:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)(=[O:9])=[O:8])=[N:28][CH:27]=1

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 59136021HCID 59136021, compound

Product 1

HCID 59136056HCID 59136056, compoundYield 93.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of N-(2-ethoxyethyl)-N-{2-[5-(hydroxymethyl)-1,3-thiazol-2-yl]-1H-indol-7-yl}thiophene-2-sulfonamide (1.00 g), N,N-dimethylformamide (1 drop) and tetrahydrofuran (15 mL) was added thionyl chloride (409 mg), 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 (970 mg, yield 93%) 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-c82d399cd759407abf357d8c0da0d197
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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