Pyridine → 1,1-dimethylethyl 7-[4-(chlorocarbonyl)phenyl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

HRID 473922Notes

Reaction equation

HRID 473922 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:14][C:13]2[CH:15]=[C:16]([C:19]3[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=3)[CH:17]=[CH:18][C:12]=2[O:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])[CH3:3].N1C=CC=CC=1.C(Cl)(=O)C([Cl:37])=O>C1(C)C=CC=CC=1.CN(C)C=O>[Cl:37][C:23]([C:22]1[CH:26]=[CH:27][C:19]([C:16]2[CH:17]=[CH:18][C:12]3[O:11][CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:4])([CH3:3])[CH3:1])=[O:7])[CH2:14][C:13]=3[CH:15]=2)=[CH:20][CH:21]=1)=[O:24]

Participants

6

Reactant 3

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 675140494-(4-{[(1,1-Dimethylethyl)oxy]carbonyl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)benzoic acid

Product 1

HCID 866720391,1-dimethylethyl 7-[4-(chlorocarbonyl)phenyl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

To a cooled (0° C.) solution of 4-(4-{[(1,1-dimethylethyl)oxy]carbonyl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)benzoic acid (0.95 g, 2.6 mmol), pyridine (1.3 mL, 15 mmol) and oxalyl chloride (0.44 mL, 5.1 mmol) in toluene (10 mL) was added dimethylformamide (0.01 mL, 0.1 mmol) and the resulting mixture was warmed to room temperature. After 24 h the reaction mixture was concentrated to provide 1,1-dimethylethyl 7-[4-(chlorocarbonyl)phenyl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (1.0 g, 100%) as a brown oil. MS (EI) for C21H22ClNO4: 388 (MH+).

Workup

  1. concentrationAfter 24 h the reaction mixture was concentrated

Sources & evidence

ORD record
ord-700bbc6b59f64fb7b58897de2684884b
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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