Tetrahydrofuran → HCID 59135658, compound

HRID 1851421Notes

Reaction equation

HRID 1851421 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 (2 drops) and tetrahydrofuran (30 mL) was stirred at room temperature overnight. 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. 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-2ee732718e34431aa31628056c127254
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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