Triethylamine → 3-(6-Benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-3-oxo-propionitrile

HRID 2224066Notes

Reaction equation

HRID 2224066 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].C(Cl)(=O)C(Cl)=O.[C:13]1([S:19]([C:22]2[CH:23]=[CH:24][C:25]3[O:30][CH2:29][CH2:28][NH:27][C:26]=3[CH:31]=2)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>ClCCl.CN(C)C=O>[C:13]1([S:19]([C:22]2[CH:23]=[CH:24][C:25]3[O:30][CH2:29][CH2:28][N:27]([C:4](=[O:6])[CH2:3][C:1]#[N:2])[C:26]=3[CH:31]=2)(=[O:21])=[O:20])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9740Cyanoacetic acidHCID 65578Oxalyl chlorideHCID 58641530HCID 58641530, compound

Product 1

HCID 586415453-(6-Benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-3-oxo-propionitrileYield 43%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of α-cyanoacetic acid (0.085 g., 1.0 mmol) in 2 mL dichloromethane was added oxalyl chloride (0.262 mL, 3.0 mmol) and one drop N,N-dimethylformamide (˜0.025 mL, cat). The solution is stirred for one hour, during which offgassing is observed, and concentrated in vacuo. The residue was dissolved in 4 mL dichloromethane and this solution was added dropwise to a solution of 6-benzenesulfonyl-3,4-dihydro-2H-benzo[1,4]oxazine (0.275 g., 1.0 mmol) and triethylamine (0.152 mL, 1.1 mmol) in 3 mL dichloromethane at 0° C. The resulting solution was stirred for 2 hours, concentrated in vacuo and purified by flash chromatography to give 0.146 g (43%) of 3-(6-benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-3-oxo-propionitrile. MS: 343 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in 4 mL dichloromethane
  3. stirringThe resulting solution was stirred for 2 hours
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-c70080df8cf543f997dd59d1e681199e
Source dataset
uspto-grants-2008_05
Patent number
US07378415B2

Reaction notes

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