Dimethylformamide → HCID 57476076, compound

HRID 1851423Notes

Reaction equation

HRID 1851423 reaction equation
[CH:1]1([CH2:4][N:5]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:22]=2[NH:21][C:20]([C:23]2[S:24][C:25]([CH2:28]O)=[CH:26][N:27]=2)=[CH:19]3)[S:6]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)(=[O:8])=[O:7])[CH2:3][CH2:2]1.CN(C)C=O.O1CCCC1.S(Cl)([Cl:42])=O>C(OCC)(=O)C.[Cl-].[Na+].O>[Cl:42][CH2:28][C:25]1[S:24][C:23]([C:20]2[NH:21][C:22]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[N:5]([CH2:4][CH:1]2[CH2:3][CH2:2]2)[S:6]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)(=[O:8])=[O:7])=[N:27][CH:26]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 59135792HCID 59135792, compound

Product 1

HCID 57476076HCID 57476076, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of N-(cyclopropylmethyl)-N-{2-[5-(hydroxymethyl)-1,3-thiazol-2-yl]-1H-indol-7-yl}thiophene-2-sulfonamide (2.15 g), N,N-dimethylformamide (0.03 mL) and tetrahydrofuran (30 mL) was added thionyl chloride (918 mg), and the mixture was stirred at room temperature for 1 hr. 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 residue was subjected to silica gel column chromatography, and eluted with ethyl acetate. The obtained solid was washed with ether-hexane (1:1) to give the title compound (2.05 g, yield 97%) as a pale-yellow solid. melting point 135° C.

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. washeluted with ethyl acetate
  6. washThe obtained solid was washed with ether-hexane (1:1)

Sources & evidence

ORD record
ord-6304d374a3334f6bbfad0af0e9e9f7be
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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