Water → HCID 178438355, compound

HRID 376255Notes

Reaction equation

HRID 376255 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]([O:23][CH:24]([F:26])[F:25])=[C:15]2[O:19][C:18]([CH:20]([CH3:22])[CH3:21])=[CH:17][C:16]=12)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[F:25][CH:24]([F:26])[O:23][C:14]1[C:15]2[O:19][C:18]([CH:20]([CH3:22])[CH3:21])=[CH:17][C:16]=2[C:11]([C:9]2[NH:8][C:7]3[CH:6]=[CH:5][N:4]=[CH:3][C:2]=3[N:1]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 19361679HCID 19361679, compound

Product 1

HCID 178438355HCID 178438355, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.8 g of N-(3-aminopyrid-4-yl)-7-difluoromethoxy-2-(1-methylethyl)benzofuran-4carboxamide are boiled with 4.0 g of p-toluenesulfonic acid in 50 ml of toluene for 3 h in a water separator. The cooled solution is extracted by shaking with 50 ml of 2 N sodium hydroxide solution, the separated aqueous phase is extracted a further two times with 50 ml of ethyl acetate each time, and the organic phases are combined, dried over ignited potassium carbonate and concentrated in vacuo. The residue is crystallized from ethanol/water. 1.7 g (100% of theory) of the title compound of m.p. 201° C. are obtained.

Workup

  1. extractionThe cooled solution is extracted
  2. extractionthe separated aqueous phase is extracted a further two times with 50 ml of ethyl acetate each time
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue is crystallized from ethanol/water

Sources & evidence

ORD record
ord-7e5b910eeae34f79a14259832b5cf27f
Source dataset
uspto-grants-2000_02
Patent number
US06020340

Reaction notes

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