4-Aminobenzenesulfonyl fluoride → HCID 22393274, compound

HRID 1071354Notes

Reaction equation

HRID 1071354 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4](Cl)[N:3]=1.[S:11]([F:21])(=[O:20])([C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1)=[O:12]>CN1C(=O)CCC1.O>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([NH:19][C:16]2[CH:17]=[CH:18][C:13]([S:11]([F:21])(=[O:20])=[O:12])=[CH:14][CH:15]=2)[N:3]=1

Participants

5

Reactant 2

HCID 668234-Aminobenzenesulfonyl fluorideHCID 28011664-Amino-2-chloropyrimidine-5-carbonitrile

Product 1

HCID 22393274HCID 22393274, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 4-amino-2-chloro-5-cyanopyrimidine (8.0 g, 52 mmol) and sulphanilyl fluoride (9.07 g, 52 mmol) in NMP (155 ml) was heated at 120° C. for 24 hours. The mixture was allowed to cool and was diluted with water. The resulting precipitate was collected by filtration, washed with water and dried under vacuum at 60° C. for 2 hours. The crude product was recrystallized from ethyl acetate/hexane to give the title compound (5.45 g, 37%). NMR: 7.70 (s, 24H), 7.93 (d, 2H), 8.15 (d, 2H), 8.45 (s, 1H); m/z: 292 (MH)+.

Workup

  1. temperatureto cool
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried under vacuum at 60° C. for 2 hours
  5. customThe crude product was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-68c7676308cf4c57aa3c272e6f76fb4b
Source dataset
uspto-grants-2005_06
Patent number
US06906065B2

Reaction notes

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