Water → 6-[2-(2,3-Dihydro-1,4-benzothiazin-4-yl)ethoxy]cyanonaphthalene

HRID 1386002Notes

Reaction equation

HRID 1386002 reaction equation
CS([O:5][CH2:6][CH2:7][N:8]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[S:11][CH2:10][CH2:9]1)(=O)=O.O[C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24](C#N)[CH:25]=2)[CH:20]=1.C(=O)([O-])[O-].[K+].[K+].O.[CH3:38][N:39](C)C=O>>[S:11]1[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:8]([CH2:7][CH2:6][O:5][C:28]2[CH:27]=[C:26]3[C:21](=[CH:20][CH:19]=2)[C:22]([C:38]#[N:39])=[CH:23][CH:24]=[CH:25]3)[CH2:9][CH2:10]1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 45894766-Hydroxy-2-naphthonitrileHCID 9921634HCID 9921634, compound

Product 1

HCID 225939256-[2-(2,3-Dihydro-1,4-benzothiazin-4-yl)ethoxy]cyanonaphthaleneYield 72%

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethyl methanesulfonate (0.49 g, 1.82 mmol), 2-hydroxy-6-cyanonaphthalene (0.28, 1.65 mmol) and potassium carbonate (1.15 g, 8.28 mmol) in dry dimethyl formamide (15 mL) was stirred at 80° C. for 12 h. Water (50 mL) was added and extracted with ethyl acetate (2×25 mL). The combined ethyl acetate layer was washed with water (25 mL), brine (20 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was chromatographed over silica gel using a mixture of ethyl acetate and pet. ether to afford the title compound (0.41 g, 72%) as a pale yellow solid. mp: 94-96° C.

Workup

  1. extractionextracted with ethyl acetate (2×25 mL)
  2. washThe combined ethyl acetate layer was washed with water (25 mL), brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was chromatographed over silica gel using
  7. additiona mixture of ethyl acetate and pet. ether

Sources & evidence

ORD record
ord-c336e5174c7d4a5dac42a36a98ac02b8
Source dataset
uspto-grants-2001_07
Patent number
US06265401B1

Reaction notes

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