Water → HCID 90315174, compound

HRID 1855208Notes

Reaction equation

HRID 1855208 reaction equation
[C:1]([C:3]1[S:4][C:5]2[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2].[CH2:13](Br)[CH:14]=[CH2:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:15]([O:12][C:10]1[CH:9]=[CH:8][C:6]2[N:7]=[C:3]([C:1]#[N:2])[S:4][C:5]=2[CH:11]=1)[CH:14]=[CH2:13]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 98819122-Cyano-6-hydroxybenzothiazole

Product 1

HCID 90315174HCID 90315174, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-cyano-6-hydroxybenzothiazole 32 (336.2 mg, 1.91 mmol) and allyl bromide (331 μl, 3.82 mmol) were dissolved in N,N-dimethylformamide (1.5 ml), potassium carbonate (404.6 mg, 1.53 mmol) was added in an argon atmosphere, and the reaction mixture was stirred for an hour at room temperature. Water (20 ml) was added to the reaction mixture, and after extraction with ethyl acetate (3×50 ml) and drying of the organic layer with anhydrous sodium sulfate, the result was concentrated in vacuo. The resulting residue was purified by preparative thin-layer silica gel column chromatography {one 20 cm×20 cm×1.75 mm plate; hexane-ethyl acetate (1:1)}, yielding 6-allyloxy-benzothiazole-2-carbonitrile 33 (418.1 mg, 90%) as a pale yellow solid.

Workup

  1. extractionafter extraction with ethyl acetate (3×50 ml)
  2. dry with materialdrying of the organic layer with anhydrous sodium sulfate
  3. concentrationthe result was concentrated in vacuo
  4. customThe resulting residue was purified by preparative thin-layer silica gel column chromatography {one 20 cm×20 cm×1.75 mm plate

Sources & evidence

ORD record
ord-4af2bec9eb084285895f5edb8735036a
Source dataset
uspto-grants-2015_02
Patent number
US08962854B2

Reaction notes

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