Chloroacetyl chloride → HCID 22665701, compound

HRID 1008536Notes

Reaction equation

HRID 1008536 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[OH:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:20][C:21](Cl)=[O:22].O1CCCC1.[H-].[Na+]>C1(C)C=CC=CC=1.O>[CH2:1]([N:8]1[CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=2[O:18][CH2:20][C:21]1=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 22665691HCID 22665691, compound

Product 1

HCID 22665701HCID 22665701, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
5 °C

Procedure

A mixture of 2.43 g of 2-(benzylamino-methyl)-4-methoxy-phenol and 20 mL of toluene was cooled to 5° C. and a solution of chloroacetyl chloride (0.88 mL) in 5 mL of toluene slowly added while stirring. Stirring was continued for 2 hours at room temperature. Dry tetrahydrofuran (25 mL) was added and 3.4 g of sodium hydride (95%; dispersion in mineral oil) were added in small portions under a nitrogen atmosphere. The mixture was allowed to stir at room temperature for 24 h. Water was added and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried (sodium sulfate) and the solvent removed in vacuo yielding 2.0 g of 4-benzyl-7-methoxy-4,5-dihydro-benzo[f][1,4]oxazepin-3-one as an oil. EI-MS: 283 (M+).

Workup

  1. stirringStirring
  2. stirringto stir at room temperature for 24 h
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried (sodium sulfate)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-def80eae14b94e65beb78a0763c44277
Source dataset
uspto-grants-2004_09
Patent number
US06797710B2

Reaction notes

Loading…