Acetyl chloride → HCID 14256342, compound

HRID 35365Notes

Reaction equation

HRID 35365 reaction equation
[O:1]1[CH2:6][CH2:5][NH:4][C@@H:3]2[CH2:7][CH2:8][O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C@@H:2]12.C(N(CC)CC)C.[C:23](Cl)(=[O:25])[CH3:24]>C(Cl)Cl>[C:23]([N:4]1[CH2:5][CH2:6][O:1][C@@H:2]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][CH2:8][CH2:7][C@@H:3]12)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 13609762trans-3,4,4a,5,6,11b-hexahydro-2H-[1]benzoxepino[5,4-b]-1,4-oxazine

Product 1

HCID 14256342HCID 14256342, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2.41 g of trans-3,4,4a,5,6,11b-hexahydro-2H-[1]benzoxepino[5,4-b]-1,4-oxazine, prepared in accordance with Example 2, and 3.5 ml of triethylamine dissolved in 50 ml of methylene chloride is added dropwise a solution of 0.85 ml of acetyl chloride dissolved in 25 ml of methylene chloride. The mixture is stirred overnight, washed with a dilute hydrochloric acid solution and dried over anhydrous magnesium sulfate. The volatiles are removed by evaporation leaving an oil which yields the compound trans-4-acetyl-3,4,4a,5,6,11b-hexahydro-2H-[1]benzoxepino[5,4-b]-1,4-oxazine having a mp. of 97°-98° C.

Workup

  1. washwashed with a dilute hydrochloric acid solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe volatiles are removed by evaporation
  4. customleaving an oil which

Sources & evidence

ORD record
ord-6a43f43d2533479aa2406cb145b3524b
Source dataset
uspto-grants-1988_08
Patent number
US04766212

Reaction notes

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