Chloroacetonitrile → 2-[4-cyanomethyl-7-fluoro-2H-1,4-benzoxazin-3(4H)-on-6-yl]-hexahydro-1H-(1,2,4)-triazolo (1,2-a)-pyridazine-1,3-dione

HRID 1381818Notes

Reaction equation

HRID 1381818 reaction equation
[F:1][C:2]1[C:12]([N:13]2[C:21](=[O:22])[N:16]3[CH2:17][CH2:18][CH2:19][CH2:20][N:15]3[C:14]2=[O:23])=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:31][C:32]#[N:33]>C(#N)C>[C:32]([CH2:31][N:6]1[C:5]2[CH:11]=[C:12]([N:13]3[C:14](=[O:23])[N:15]4[CH2:20][CH2:19][CH2:18][CH2:17][N:16]4[C:21]3=[O:22])[C:2]([F:1])=[CH:3][C:4]=2[O:9][CH2:8][C:7]1=[O:10])#[N:33]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 144028742-[7-fluoro-2H-1,4-benzoxazin-3(4H)-on-6-yl]-hexahydro-1H-(1,2,4)-triazolo (1,2-a) pyridazine-1,3-dione

Product 1

HCID 144028832-[4-cyanomethyl-7-fluoro-2H-1,4-benzoxazin-3(4H)-on-6-yl]-hexahydro-1H-(1,2,4)-triazolo (1,2-a)-pyridazine-1,3-dioneYield 70.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture composed of 2-[7-fluoro-2H-1,4-benzoxazin-3(4H)-on-6-yl]-hexahydro-1H-(1,2,4)-triazolo (1,2-a)-pyridazine-1,3-dione (2.04 g), potassium carbonate (1.06 g), chloroacetonitrile (0.96 g) and acetonitrile (30 ml) is refluxed for 3 hours. The reaction mixture is made free from acetonitrile by evaporation in vacuo and mixed with water. The resultant solid is collected by filtration and washed with a small amount of ethanol to obtain an end product 2-[4-cyanomethyl-7-fluoro-2H-1,4-benzoxazin-3(4H)-on-6-yl]-hexahydro-1H-(1,2,4)-triazolo (1,2-a)-pyridazine-1,3-dione (1.62 g),

Workup

  1. temperatureis refluxed for 3 hours
  2. customThe reaction mixture is made free from acetonitrile by evaporation in vacuo
  3. additionmixed with water
  4. filtrationThe resultant solid is collected by filtration
  5. washwashed with a small amount of ethanol

Sources & evidence

ORD record
ord-1817e246e0bf4aa1bf9addaf6b5208f4
Source dataset
uspto-grants-1989_02
Patent number
US04804394

Reaction notes

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