Chloroacetyl chloride → 6-Chloro-2H-1,4-benzoxazin-3(4H)-one

HRID 355357Notes

Reaction equation

HRID 355357 reaction equation
Cl[CH2:2][C:3](Cl)=[O:4].[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([OH:14])=[C:11]([CH:13]=1)[NH2:12].C(=O)(O)[O-].[Na+]>ClCCl.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[O:14][CH2:2][C:3](=[O:4])[NH:12][C:11]=2[CH:13]=1

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 72652-Amino-4-chlorophenolHCID 516892Sodium Bicarbonate

Product 1

HCID 3092596-Chloro-2H-1,4-benzoxazin-3(4H)-oneYield 93%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Chloroacetyl chloride (2.39 ml) in dichloromethane (25 ml) was added to a mixture of 5-chloro-2-hydroxyaniline (3.59 g), triethyl benzylammonium chloride (5.7 g) and sodium bicarbonate (8.4 g) in dichloromethane (100 ml) at 0°C. After the addition the mixture was heated to reflux for 4 hours, then cooled and concentrated. The residue was treated with water and the resultant solid washed with ether to give 6-chloro-benzo[1,4]oxazin-3-one (4.2 g, 93% yield) as a buff coloured solid; 1H NMR (270 Mz): 3.2(1H,brd), 4.42(2H,s), 6.8-7.0(3H,m) ppm.

Workup

  1. additionAfter the addition the mixture
  2. temperaturewas heated
  3. temperatureto reflux for 4 hours
  4. temperaturecooled
  5. concentrationconcentrated
  6. additionThe residue was treated with water
  7. washthe resultant solid washed with ether

Sources & evidence

ORD record
ord-d79df8b46f504bc8b2347c9e25241431
Source dataset
uspto-grants-1998_11
Patent number
US05830890

Reaction notes

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