4-Aminobenzenesulfonyl fluoride → HCID 86590241, compound

HRID 1071944Notes

Reaction equation

HRID 1071944 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH3:10])[C:5]([C:11]#[N:12])=[CH:4][N:3]=1.[S:13]([F:23])(=[O:22])([C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1)=[O:14]>CC(O)CC>[C:11]([C:5]1[C:6]([NH:8][CH2:9][CH3:10])=[N:7][C:2]([NH:21][C:18]2[CH:19]=[CH:20][C:15]([S:13]([F:23])(=[O:22])=[O:14])=[CH:16][CH:17]=2)=[N:3][CH:4]=1)#[N:12]

Participants

4

Reactant 2

HCID 668234-Aminobenzenesulfonyl fluorideHCID 223906122-Chloro-5-cyano-4-ethylaminopyrimidine

Product 1

HCID 86590241HCID 86590241, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6568(+-)-2-ButanolSolvent

Procedure

2-Chloro-5-cyano-4-ethylaminopyrimidine (Method 56; 6.35 g, 34.88 mmol) and sulphanilyl fluoride (6.11 g, 34.88 mmol) in 2-butanol (120 ml) were heated at 95° C. for 4 hours and then stirred at ambient temperatures for 48 hours. The volatiles were evaporated and the residue triturated with ether to give the title compound (10.46 g, 93%). NMR: 1.20 (t, 3H), 3.45 (m, 2H), 8.00 (d, 2H), 8.13 (d, 2H), 8.41 (s, 1H), 10.52 (s, 1H); m/z: 321.

Workup

  1. customThe volatiles were evaporated
  2. customthe residue triturated with ether

Sources & evidence

ORD record
ord-b5240c17b5614954b0af57279c7aed66
Source dataset
uspto-grants-2005_06
Patent number
US06908920B2

Reaction notes

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