Diethylamine → HCID 54176686, compound

HRID 1415672Notes

Reaction equation

HRID 1415672 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[S:9]([N:12]=[C:13]=[O:14])(=[O:11])=[O:10].[CH:15]([N:18](C(C)C)[CH2:19][CH3:20])(C)[CH3:16].C(NCC)C>C(#N)C>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:13]([NH:12][S:9]([N:18]([CH2:19][CH3:20])[CH2:15][CH3:16])(=[O:11])=[O:10])=[O:14]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 104392-AminopyridineHCID 70918Chlorosulfonyl isocyanateHCID 81531Diisopropylethylamine2×

Product 1

HCID 54176686HCID 54176686, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

This example was prepared according to the general procedure described by Karady et al. in Heterocycles, 1979, 12, 815-818. To a solution of 2-aminopyridine (5.0 g, 0.053 mol) in acetonitrile (17.5 mL) cooled to 0° C. was added chlorosulfonylisocyanate (4.5 mL) while maintaining the temperature between -5 and +5° C. A very thick precipitate formed. The cooling bath was removed, and the reaction mixture was allowed to warm to room temperature. The mixture was re-cooled to 0° C., and diisopropylethylamine (8 mL, 0.046 mol) was added dropwise with stirring while maintaining the internal temperature between -5 and +5° C. An additional 0.85 mL of diisopropylethylamine was added, and the mixture was allowed to warm to room temperature and stirred overnight. The solid that formed was filtered, washed with cold acetonitrile, and dried in vacuo; yield 6.0 g. To a mixture of this 1,2,4,6-thiatriazene-1,1-dioxide (2.0 g, 0.010 mol) in acetonitrile (60 mL) was added diethylamine (0.97 mL, 9.38 mmol). The reaction mixture was stirred overnight at room temperature and evaporated. The resulting solid was triturated with methanol, filtered, washed with diethyl ether, and dried in vacuo; yield 1.6 g (55%).

Workup

  1. temperaturewhile maintaining the temperature between -5 and +5° C
  2. customA very thick precipitate formed
  3. customThe cooling bath was removed
  4. temperatureThe mixture was re-cooled to 0° C.
  5. temperaturewhile maintaining the internal temperature between -5 and +5° C
  6. temperatureto warm to room temperature
  7. stirringstirred overnight
  8. customThe solid that formed
  9. filtrationwas filtered
  10. washwashed with cold acetonitrile
  11. customdried in vacuo
  12. stirringThe reaction mixture was stirred overnight at room temperature
  13. customevaporated
  14. customThe resulting solid was triturated with methanol
  15. filtrationfiltered
  16. washwashed with diethyl ether
  17. customdried in vacuo

Sources & evidence

ORD record
ord-9f6e80e2b16a49fca9b93442e0c53246
Source dataset
uspto-grants-1999_06
Patent number
US05908842

Reaction notes

Loading…