Acetyl chloride → HCID 10753523, compound

HRID 2081554Notes

Reaction equation

HRID 2081554 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]([OH:14])=[O:13])[C:5]2[O:10][CH2:9][CH2:8][NH:7][C:6]=2[CH:11]=1.C(N(CC)CC)C.[C:22](Cl)(=[O:24])[CH3:23].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[C:22]([N:7]1[C:6]2[CH:11]=[C:2]([Cl:1])[CH:3]=[C:4]([C:12]([OH:14])=[O:13])[C:5]=2[O:10][CH2:9][CH2:8]1)(=[O:24])[CH3:23]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 106086516-Chloro-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylic acid

Product 1

HCID 10753523HCID 10753523, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 10 g of 6-chloro-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylic acid and 6.5 ml of triethylamine in 100 ml of chloroform was cooled, and 4.4 g of acetyl chloride was added thereto with stirring. The resulting mixture was stirred at room temperature for 2 hours. To the liquid reaction mixture were added an aqueous solution of sodium hydrogen carbonate and chloroform, and the resulting organic layer was separated, washed with water, and then dried with magnesium sulfate. The solvent was distilled off under reduced pressure, thereby obtaining 7.8 g of 4-acetyl-6-chloro-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylic acid. Melting point: 76°-77° C.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 2 hours
  2. customTo the liquid reaction mixture
  3. customthe resulting organic layer was separated
  4. washwashed with water
  5. dry with materialdried with magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-017b71274f0e4c449f3f5ba9ab26b240
Source dataset
uspto-grants-1993_02
Patent number
US05185333

Reaction notes

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