Dimethylformamide → HCID 22665722, compound

HRID 2304276Notes

Reaction equation

HRID 2304276 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:18][C:19](Cl)=[O:20].CN(C)C=O.[H-].[Na+]>C1(C)C=CC=CC=1.O>[CH2:1]([N:8]1[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH2:18][C:19]1=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6577Chloroacetyl chlorideHCID 24758Sodium hydrideHCID 408360HCID 408360, compound

Product 1

HCID 22665722HCID 22665722, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 19.0 g of 2-(benzylamino-methyl)-phenol and 75 mL of toluene was cooled to 0° C., and a solution of chloroacetyl chloride (7.8 mL) in 75 mL of toluene was slowly added while stirring. Stirring was continued for 16 h. Dry N,N-dimethylformamide (60 mL) was added and the solution was cooled to 0° C. In a nitrogen atmosphere 3.4 g of sodium hydride (95%; dispersion in mineral oil) were added in small portions and the mixture was allowed to stir at room temperature for 2 h. Water was added and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried (sodium sulfate) and the solvent was removed in vacuo yielding 12.4 g of 4-benzyl-4,5-dihydro-benzo[f][1,4]oxazepin-3-one. M.p. 95-97° C., EI-MS: 253 (M+).

Workup

  1. stirringStirring
  2. temperaturethe solution was cooled to 0° C
  3. stirringto stir at room temperature for 2 h
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried (sodium sulfate)
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f721ff9fe7a74c4a96c4db5089ad7a4f
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

Loading…