Chloroacetyl chloride → HCID 69915983, compound

HRID 1835045Notes

Reaction equation

HRID 1835045 reaction equation
[NH2:1][C:2]1[C:7]2[NH:8][C:9](=[O:12])[CH2:10][O:11][C:6]=2[CH:5]=[C:4]([F:13])[C:3]=1[N:14]1[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]([CH3:25])[C:15]1=[O:26].[Cl:27][CH2:28][C:29](Cl)=[O:30]>O1CCOCC1>[Cl:27][CH2:28][C:29]([NH:1][C:2]1[C:7]2[NH:8][C:9](=[O:12])[CH2:10][O:11][C:6]=2[CH:5]=[C:4]([F:13])[C:3]=1[N:14]1[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]([CH3:25])[C:15]1=[O:26])=[O:30]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 23502535HCID 23502535, compound

Product 1

HCID 69915983HCID 69915983, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-[5-Amino-7-fluoro-2H-1,4-benzoxazine-3(4H)-on-6-yl]-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione (400 mg, 1.07 mmol) was dissolved in anhydrous dioxane and chloroacetyl chloride (135.6 mg, 1.20 mmol) was added. Solution was heated to reflux for 2 hr and solvent removed in vacuo. The residue was washed with ether to afford the title compound (351.9 mg, 0.78 mmol).

Workup

  1. temperatureSolution was heated
  2. temperatureto reflux for 2 hr
  3. customsolvent removed in vacuo
  4. washThe residue was washed with ether

Sources & evidence

ORD record
ord-4c99001d112a43aabad8e3518a0f8110
Source dataset
uspto-grants-2004_08
Patent number
US06770596B1

Reaction notes

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