Benzoyl chloride → HCID 12881972, compound

HRID 1577988Notes

Reaction equation

HRID 1577988 reaction equation
[CH:1]1[C:6]2[CH2:7][NH:8][C:9]3[CH:15]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:13]=[CH:12][C:10]=3[O:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>N1C=CC=CC=1.C(Cl)(Cl)Cl>[C:21]([N:8]1[CH2:7][C:6]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[O:11][C:10]2[CH:12]=[CH:13][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:15][C:9]1=2)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 12881938HCID 12881938, compound

Product 1

HCID 12881972HCID 12881972, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent2×

Procedure

To a solution of ethyl 10,11-dihydrodibenz[b,f][1,4]oxazepine-8-carboxylate (1.35 g) in a mixture of pyridine (2.5 ml) and chloroform (5 ml) was added dropwise a solution of benzoyl chloride (0.7 g) in chloroform (5 ml) over 15 minutes while stirring under ice cooling. The resulting mixture was stirred at room temperature for 3 hours, washed with a diluted sodium hydroxide aqueous solution and with water, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove chloroform. The residue was recrystallized from ethanol to give ethyl N-benzoyl-10,11-dihydrodibenz[b,f][1,4]oxazepine-8-carboxylate as colorless needles.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 3 hours
  2. washwashed with a diluted sodium hydroxide aqueous solution and with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove chloroform
  6. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-acfeb5503a8d40729f2b5a00800fc900
Source dataset
uspto-grants-1981_09
Patent number
US04290953

Reaction notes

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