Imidazole → HCID 13726519, compound

HRID 1981745Notes

Reaction equation

HRID 1981745 reaction equation
Cl[CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH3:11])[C:8](=[O:12])[C:7]2[CH:13]=[CH:14][CH:15]=[N:16][C:6]=2[O:5]1.[NH:17]1[CH:21]=[CH:20][N:19]=[CH:18]1>CN(C)C=O>[N:17]1([CH2:2][CH2:3][CH:4]2[CH2:10][N:9]([CH3:11])[C:8](=[O:12])[C:7]3[CH:13]=[CH:14][CH:15]=[N:16][C:6]=3[O:5]2)[CH:21]=[CH:20][N:19]=[CH:18]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 137264362-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepine-5(4H)-one

Product 1

HCID 13726519HCID 13726519, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepine-5(4H)-one, 9.12 g (0.038 mole) in dimethylformamide (30 ml) was added imidazole, 5.66 g (0.083 mole). The solution was heated to 130° C. for 18 hr. Dimethylformamide was removed by rotary evaporation (80° C., vacuum pump) and the residue taken up in chloroform (100 ml). The chloroform was washed with dilute aqueous sodium hydroxide (30 ml), dried over sodium sulfate and concentrated by rotary evaporation (70° C., water aspirator) to an oil. Crystallization was induced with ethanol. White crystals, 1.5 g (14.5%) were collected, m.p. 150°-152° C.

Workup

  1. customDimethylformamide was removed by rotary evaporation (80° C., vacuum pump)
  2. washThe chloroform was washed with dilute aqueous sodium hydroxide (30 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated by rotary evaporation (70° C., water aspirator) to an oil
  5. customCrystallization
  6. customWhite crystals, 1.5 g (14.5%) were collected

Sources & evidence

ORD record
ord-7b1bbce00aa14ab5852f068283303dca
Source dataset
uspto-grants-1986_06
Patent number
US04592866

Reaction notes

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