Pyridine → HCID 86659803, compound

HRID 1846289Notes

Reaction equation

HRID 1846289 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].N1C=CC=CC=1.Cl[C:22](Cl)([O:24]C(=O)OC(Cl)(Cl)Cl)Cl>C(#N)C.ClCCl>[CH3:14][S:11]([C:9]1[CH:8]=[CH:7][C:3]2[C:4](=[O:6])[O:5][C:22](=[O:24])[NH:1][C:2]=2[CH:10]=1)(=[O:13])=[O:12]

Participants

6

Reactant 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 27610582-Amino-4-(methylsulfonyl)benzoic acid

Product 1

HCID 86659803HCID 86659803, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
55 °C

Procedure

To a suspension of 2-amino-4-methanesulfonyl-benzoic acid (1.00 g, 4.64 mmol) in acetonitrile (15 mL) at 55° C. were simultaneously added pyridine (0.75 mL, 9.3 mmol) and a solution of triphosgene (0.455 g, 1.53 mmol) in dichloromethane (5 mL). The resulting mixture was stirred at 55° C. for 2 hours and the solvent was removed using a rotary evaporator. The residue was diluted with water (50 mL) and the precipitate was filtered, and air dried to provide 7-methanesulfonyl-1H-benzo[d][1,3]oxazine-2,4-dione. Yield: 0.98 g (82%).

Workup

  1. customthe solvent was removed
  2. customa rotary evaporator
  3. additionThe residue was diluted with water (50 mL)
  4. filtrationthe precipitate was filtered
  5. customair dried

Sources & evidence

ORD record
ord-8094f41f1bcd4d3c8b6c27f81c5044de
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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