Sodium Hydroxide → HCID 86049102, compound

HRID 2235516Notes

Reaction equation

HRID 2235516 reaction equation
[C:1]1([CH3:23])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH:9][C:10]1[S:11][C:12]2[C:18]([N+:19]([O-])=O)=[CH:17][C:16]([CH3:22])=[CH:15][C:13]=2[N:14]=1.O.O.[Sn](Cl)Cl.[OH-].[Na+]>CN(C=O)C>[C:1]1([CH3:23])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH:9][C:10]1[S:11][C:12]2[C:18]([NH2:19])=[CH:17][C:16]([CH3:22])=[CH:15][C:13]=2[N:14]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 86049098HCID 86049098, compound

Product 1

HCID 86049102HCID 86049102, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N-mesityl-5-methyl-7-nitro-1,3-benzothiazol-2-amine (45 mg, 0.137 mmol) and tin(II) chloride dihydrate (124 mg, 0.550 mmol) in DMF (2 ml) was heated at 80° C. for 1 h. The mixture was poured into ice and the pH was made slightly basic (pH 7-8) by addition of 1N NaOH solution. The aqueous solution was extracted with AcOEt. The extract was washed with brine, dried over magnesium sulfate and concentrated under vacuum. The residue was purified by chromatography eluting with 20% AcOEt in n-hexane to afford 10 mg of the title compound.

Workup

  1. additionThe mixture was poured into ice
  2. extractionThe aqueous solution was extracted with AcOEt
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by chromatography
  7. washeluting with 20% AcOEt in n-hexane

Sources & evidence

ORD record
ord-0769ae60f62549ac9411057a5b1d2221
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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