Tetrahydrofuran → HCID 59135658, compound

HRID 1960252Notes

Reaction equation

HRID 1960252 reaction equation
O[CH2:2][C:3]1[S:7][C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][C:11]=3[N:17]([CH:26]([CH3:28])[CH3:27])[S:18]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)(=[O:20])=[O:19])=[N:5][CH:4]=1.S(Cl)([Cl:31])=O.O1CCCC1>CN(C)C=O.O>[Cl:31][CH2:2][C:3]1[S:7][C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][C:11]=3[N:17]([CH:26]([CH3:28])[CH3:27])[S:18]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)(=[O:20])=[O:19])=[N:5][CH:4]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 59135949HCID 59135949, compound

Product 1

HCID 59135658HCID 59135658, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 962WaterSolvent

Procedure

A mixture of N-{2-[5-(hydroxymethyl)-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-isopropylthiophene-2-sulfonamide (2.12 g), thionyl chloride (0.70 ml), N,N-dimethylformamide (two drop) and tetrahydrofuran (30 ml) was stirred overnight at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with saturated brine, aqueous sodium bicarbonate and saturated brine, dried (MgSO4), and concentrated. The residue was crystallized from diethyl ether, and the crystals were collected by filtration, washed with diethyl ether, and dried to give the title compound (2.00 g, yield 90%) as yellow crystals. melting point 184-185° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed successively with saturated brine, aqueous sodium bicarbonate and saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was crystallized from diethyl ether
  6. filtrationthe crystals were collected by filtration
  7. washwashed with diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-39324b74711049c78edb4c1096b0a2c9
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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