Tetrahydrofuran → HCID 86049092, compound

HRID 2235513Notes

Reaction equation

HRID 2235513 reaction equation
[C:1]1([CH3:26])[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-:21])=[O:20])=[CH:17][C:16]([C:22](OC)=[O:23])=[CH:15][C:13]=2[N:14]=1.[BH4-].[Li+].O1CCCC1>C(OCC)C>[C:1]1([CH3:26])[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-:21])=[O:20])=[CH:17][C:16]([CH2:22][OH:23])=[CH:15][C:13]=2[N:14]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 86612992HCID 86612992, compound

Product 1

HCID 86049092HCID 86049092, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of methyl 2-mesitylamino-7-nitro-1,3-benzothiazole-5-carboxylate (350 mg, 0.942 mmol) in ethyl ether (6 ml) was added 2.0 M solution of lithium borohydride in tetrahydrofuran (THF) (1.41 ml, 2.82 mmol). The mixture was stirred at room temperature for 15 h. The reaction was quenched with saturated NH4Cl solution. The aqueous phase was extracted with ethyl ether. 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 189 mg of the title compound.

Workup

  1. customThe reaction was quenched with saturated NH4Cl solution
  2. extractionThe aqueous phase was extracted with ethyl ether
  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-2fb3a0a857454691bb8487d33655fb44
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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