1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 14304453, compound

HRID 477731Notes

Reaction equation

HRID 477731 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][S:10]([C:13]1[N:17]=[CH:16][NH:15][N:14]=1)(=[O:12])=[O:11].C1(C)C=CC(S([C:27]2[N:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH3:34])[N:28]=2)(=O)=O)=CC=1.N12CCCN=C1CCCCC2>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][S:10]([C:13]1[N:17]=[CH:16][N:15]([C:27]2[N:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH3:34])[N:28]=2)[N:14]=1)(=[O:11])=[O:12]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 14304452HCID 14304452, compoundHCID 178527547HCID 178527547, compound

Product 1

HCID 14304453HCID 14304453, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(2,6-dichlorophenyl)-1,2,4-triazole-3-sulphonamide (2.051 g) was heated for 1 hour at 125° C. with 1.82 g of 2-p-toluenesulphonyl-4,6-dimethylpyrimidine in the presence of 1,8-diazabicyclo(5,4,0)undec-7-ene (2.128 g) in dimethylformamide (35 ml). After distillation of the solvent, the residue was poured into a mixture of water (80 ml) and 1N hydrochloric acid (20 ml), and was then filtered off. This crude product was chromatographed on silica gel using methylene chloride/methanol (95/5) as eluent, to give 2.2 g of the desired product, mp 274°-275° C.

Workup

  1. distillationAfter distillation of the solvent
  2. additionthe residue was poured into a mixture of water (80 ml) and 1N hydrochloric acid (20 ml)
  3. filtrationwas then filtered off
  4. customThis crude product was chromatographed on silica gel

Sources & evidence

ORD record
ord-f771854aabdd436bb6ff5f34a3410c88
Source dataset
uspto-grants-1989_12
Patent number
US04889553

Reaction notes

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