2-Methylbenzenesulfonamide → HCID 19603692, compound

HRID 1604653Notes

Reaction equation

HRID 1604653 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][C:20]4[S:21][CH:22]=[C:23]([C:25](O)=[O:26])[N:24]=4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[S:35]([NH2:38])(=[O:37])=[O:36].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.CN(C)C=O>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][C:20]4[S:21][CH:22]=[C:23]([C:25](=[O:26])[NH:38][S:35]([C:30]5[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=5[CH3:28])(=[O:36])=[O:37])[N:24]=4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 69242-MethylbenzenesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19603666HCID 19603666, compound

Product 1

HCID 19603692HCID 19603692, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-tert-butyl-2-{5-[(4-carboxythiazol-2-yl)methyl]benzofuran-2-yl}thiazole (0.20 g), 2-methylbenzenesulfonamide (0.10 g), 4-dimethylaminopyridine (0.12 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.19 g) in N,N-dimethylformamide (6 ml) was stirred at ambient temperature for 2 days. The resulting mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with ethyl acetate. The fractions containing object compound were combined and concentrated under reduced pressure. The residue was crystallized from diethyl ether and filtered to give 4-tert-butyl-2-{5-{{4-[N-(2-methylphenylsulfonyl)carbamoyl]thiazol-2-yl}methyl}-benzofuran-2-yl}thiazole (0.18 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in reduced pressure
  5. washeluted with ethyl acetate
  6. additionThe fractions containing object compound
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from diethyl ether
  9. filtrationfiltered

Sources & evidence

ORD record
ord-a92eb9877ba74ee1b531d1b5ed7de204
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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