2-Thiophenesulfonyl chloride → HCID 54248503, compound

HRID 620658Notes

Reaction equation

HRID 620658 reaction equation
[NH2:1][C:2]1[N:12]=[C:5]2[N:6]=[C:7]([CH3:11])[CH:8]=[C:9]([CH3:10])[N:4]2[N:3]=1.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[S:18](Cl)(=[O:20])=[O:19]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH3:11][C:7]1[CH:8]=[C:9]([CH3:10])[N:4]2[N:3]=[C:2]([NH:1][S:18]([C:14]3[S:13][CH:17]=[CH:16][CH:15]=3)(=[O:20])=[O:19])[N:12]=[C:5]2[N:6]=1

Participants

5

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 2673105,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-2-amine

Product 1

HCID 54248503HCID 54248503, compoundYield 6.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 4.24 g (26.0 mmol) of 2-amino-5,7-dimethyl-1,2,4-triazolo(1,5-a)pyrimidine, 5.08 g (27.8 mmol) of 2-thiophene sulfonyl chloride and 0.16 g (1.3 mmol) of 4-dimethylaminopyridine in 30 ml of dry pyridine was heated at reflux for 47 hours. The majority of the pyridine was removed by evaporation at reduced pressure and the residue was taken up in 1N NaOH, treated with charcoal and filtered through celite. The filtrated was treated with charcoal and filtered through celite. The yellow filtrate was cooled in an ice bath and acidified with concentrated HCl to precipitate a yellow solid. Drying in vacuo gave 0.50 g (6 percent) of the desired sulfonamide as a yellow powder, m.p. 236°-237.5° C.: IR (KBr) 3390 (broad), 1493, 1375 and 1156 cm-1 ; 'H NMR (DMSO-d6) δ12.3 (1H, broad, --SO2NH--), 7.7-8.1 (2H, m, thiophene H's at 3- and 5-positions), 6.9-7.3 (2H, m including S at 7.03, thiophene H at 4-position and pyrimidine H), 2.62 (3H, s, --CH3) and 2.49 (3H, s, --CH3).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 47 hours
  3. customThe majority of the pyridine was removed by evaporation at reduced pressure
  4. additiontreated with charcoal
  5. filtrationfiltered through celite
  6. additionThe filtrated was treated with charcoal
  7. filtrationfiltered through celite
  8. temperatureThe yellow filtrate was cooled in an ice bath
  9. customto precipitate a yellow solid
  10. customDrying in vacuo

Sources & evidence

ORD record
ord-3085313c76004af08533cf7a99b1005c
Source dataset
uspto-grants-1989_04
Patent number
US04822404

Reaction notes

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