Acetic Acid → HCID 86601176, compound

HRID 723084Notes

Reaction equation

HRID 723084 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([N+]([O-])=O)=[C:8]([S:10]([C:13]2[CH:14]=[N:15][C:16]([Br:20])=[C:17]([Cl:19])[CH:18]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4].[CH3:24][S-:25].[Na+].C(O)(=O)C>>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([S:25][CH3:24])=[C:8]([S:10]([C:13]2[CH:14]=[N:15][C:16]([Br:20])=[C:17]([Cl:19])[CH:18]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 4378561Sodium methanethiolateHCID 86601177HCID 86601177, compound

Product 1

HCID 86601176HCID 86601176, compoundYield 23%

Procedure

The procedure described in Example 27: step a was followed using 4-(6-Bromo-5-chloro-pyridine-3-sulfonyl)-5-nitro-thiophene-2-carboxylic acid methyl ester (63 mg, 0.14 mmol, Example 123: step b) and sodium thiomethoxide (0.5 M in EtOH, 0.18 mmol, 360 μL). The reaction was quenched with acetic acid (10 uL, 0.18 mol) followed by concentration in vacuo. The residue was then dissolved into EtOAc and washed with saturated NaHCO3 and brine solutions. The organic layers were dried (Na2SO4) and removal of the solvents in vacuo was followed by purification by preparative SiO2 TLC (30% EtOAc in hexanes) that yielded the title compound (14.2 mg, 23%) as a yellow solid. ESI-MS (m/z): Calcd. for C12H9BrClNO4S3: 441.9 (M+1) found: 442.0.

Workup

  1. concentrationfollowed by concentration in vacuo
  2. dissolutionThe residue was then dissolved into EtOAc
  3. washwashed with saturated NaHCO3 and brine solutions
  4. customThe organic layers were dried
  5. custom(Na2SO4) and removal of the solvents in vacuo
  6. customwas followed by purification by preparative SiO2 TLC (30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4e678f9b6dca41f79367e4a9f77c75d4
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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