Dimethylformamide → 7-Chloro-9-(1-chloroethyl)-6-methyl-3,4-dihydro-1,4-benzoxazepin-5(2H)-one

HRID 626825Notes

Reaction equation

HRID 626825 reaction equation
N1C(Cl)=NC(Cl)=NC=1[Cl:3].[Cl:10][C:11]1[CH:12]=[C:13]([CH:24](O)[CH3:25])[C:14]2[O:20][CH2:19][CH2:18][NH:17][C:16](=[O:21])[C:15]=2[C:22]=1[CH3:23].CN(C)C=O>C(Cl)Cl>[Cl:10][C:11]1[CH:12]=[C:13]([CH:24]([Cl:3])[CH3:25])[C:14]2[O:20][CH2:19][CH2:18][NH:17][C:16](=[O:21])[C:15]=2[C:22]=1[CH3:23]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7954Cyanuric chlorideHCID 866975197-Chloro-9-(1-hydroxyethyl)-6-methyl-3,4-dihydro-1,4-benzoxazepin-5(2H)-one

Product 1

HCID 866975207-Chloro-9-(1-chloroethyl)-6-methyl-3,4-dihydro-1,4-benzoxazepin-5(2H)-oneYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of cyanuric chloride (15 mg, 0.079 mmol), 7-chloro-9-(1-hydroxyethyl)-6-methyl-3,4-dihydro-1,4-benzoxazepin-5(2H)-one (14 mg, 0.053 mmol) and N,N-dimethylformamide (20 μL) in methylene chloride (0.4 mL) was stirred at room temperature overnight. The mixture was diluted with methylene chloride, washed with saturated sodium bicarbonate, water, brine, dried over sodium sulfate, filtered and concentrated to give the desired compound (10 mg, 70%).

Workup

  1. washwashed with saturated sodium bicarbonate, water, brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4540b44b21964430bed0a6c1e28e027a
Source dataset
uspto-grants-2016_04
Patent number
US09309251B2

Reaction notes

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