Acetyl chloride → HCID 13060519, compound

HRID 354850Notes

Reaction equation

HRID 354850 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:13](Cl)(=O)[O:14]CC.C(Cl)(=O)C>CCCCCC>[CH2:11]([C:8]1[CH:9]=[CH:10][C:2]2[NH:1][C:13](=[O:14])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=1)[CH3:12]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 10928Ethyl chloroformateHCID 77444862-Amino-5-ethylbenzoic acid

Product 1

HCID 13060519HCID 13060519, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-amino-5-ethylbenzoic acid (20.28 g) and ethyl chlorocarbonate (53.5 g) was stirred for 50 minutes at 100° C. and then cooled to 90° C. To the mixture was added dropwise acetyl chloride (13.81 g) in the course of 15 minutes and the reaction mixture was stirred for 2 hours at 100° C. After the resultant mixture was cooled to ambient temperature, to the mixture was added hexane and allowed to stand at ambient temperature to give crystals, which were separated by filtration, washed with hexane and dried under reduced pressure to give crystalline 6-ethyl-2H-3,1-benzoxazine-2,4(1H)-dione (19.55 g).

Workup

  1. temperaturecooled to 90° C
  2. stirringthe reaction mixture was stirred for 2 hours at 100° C
  3. customto stand at ambient temperature
  4. customto give crystals, which
  5. customwere separated by filtration
  6. washwashed with hexane
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-401ec39afd5d49da885a8df14a29024f
Source dataset
uspto-grants-1983_03
Patent number
US04377580

Reaction notes

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