Hydrochloric Acid → 3-[(2-Methyl-1-Imidazolyl)Methyl]-4-Oxo-9-Methysulfonyl-2,3,4,9-Tetrahydrothiopyrano[2,3-b]Indole

HRID 1086518Notes

Reaction equation

HRID 1086518 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:5]([CH2:9][CH:10]2[CH2:22][S:21][C:13]3[NH:14][C:15]4[C:20]([C:12]=3[C:11]2=[O:23])=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH:6]=[CH:7][N:8]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26].C(=O)([O-])[O-].[Na+].[Na+].Cl>CN(C)C=O.C(O)C>[CH3:3][C:4]1[N:5]([CH2:9][CH:10]2[CH2:22][S:21][C:13]3[N:14]([S:25]([CH3:24])(=[O:27])=[O:26])[C:15]4[C:20]([C:12]=3[C:11]2=[O:23])=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH:6]=[CH:7][N:8]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 198261563-[(2-Methyl-1-Imidazolyl)Methyl]-4-Oxo-2,3,4,9-Tetrahydrothiopyrano[2,3-b]Indole

Product 1

HCID 198261863-[(2-Methyl-1-Imidazolyl)Methyl]-4-Oxo-9-Methysulfonyl-2,3,4,9-Tetrahydrothiopyrano[2,3-b]Indole

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

0.20 g (0.0042 mol) of sodium hydride, at a concentration of 50% in oil, is added in the course of 30 minutes and under a nitrogen atmosphere to a solution of 1.19 g (0.004 mol) of 3-[(2-methyl-1-imidazolyl)methyl]-4-oxo-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole in 20 ml of dimethylformamide, and 0.325 ml (0.0042 mol) of methanesulfonyl chloride is then added. The mixture is stirred for 4 hours at room temperature, 150 ml of 2N sodium carbonate solution are added and the resulting mixture is extracted three times with ethyl acetate. The organic phases are combined, dried and evaporated. The residue (1.35 g) is chromatographed on silica gel, eluting with a methylene chloride/ethanol mixture (92:8). The residue obtained is dissolved in 20 ml of ethanol and the solution is treated with 3 ml of an ethereal solution of hydrochloric acid at 10° C. for 1 hour. The precipitate is drained, washed with ethyl ether and recrystallized in acetonitrile.

Workup

  1. additionis then added
  2. extractionthe resulting mixture is extracted three times with ethyl acetate
  3. customdried
  4. customevaporated
  5. customThe residue (1.35 g) is chromatographed on silica gel
  6. washeluting with a methylene chloride/ethanol mixture (92:8)
  7. customThe residue obtained
  8. washwashed with ethyl ether
  9. customrecrystallized in acetonitrile

Sources & evidence

ORD record
ord-f984b927ee47447e8f652fcf29e96c8a
Source dataset
uspto-grants-1991_07
Patent number
US05030646

Reaction notes

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