Water → HCID 58994992, compound

HRID 536959Notes

Reaction equation

HRID 536959 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:18]#[N:19])[CH2:15][CH2:14][S:13](=[O:17])(=[O:16])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH2:20]>C(O)C.CCOC(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:18]([NH2:19])=[O:20])[CH2:11][CH2:12][S:13](=[O:17])(=[O:16])[CH2:14][CH2:15]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 962WaterHCID 589949324-(4-Nitro-phenyl)-1,1-dioxo-hexahydro-1lambda6-thiopyran-4-carbonitrile

Product 1

HCID 58994992HCID 58994992, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(4-nitro-phenyl)-1,1-dioxo-hexahydro-1λ6-thiopyran-4-carbonitrile (as prepared in the previous step) in ethanol and water is treated with NaBO3 (Synthetic Communications, 20(4), 563-71, (1990)). The mixture is diluted with EtOAc and washed with water. The organic layer is dried (MgSO4) and concentrated in vacuo. The residue is purified by silica gel chromatography with the appropriate solvent to afford the title compound.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer is dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by silica gel chromatography with the appropriate solvent

Sources & evidence

ORD record
ord-8c9c09d3c51e45d2b8f0a22d9101632f
Source dataset
uspto-grants-2014_10
Patent number
US08859602B2

Reaction notes

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