Triethylamine → 5'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl dimethylsulfamate

HRID 418418Notes

Reaction equation

HRID 418418 reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[C:10]([C:20]#[N:21])=[CH:9][CH:8]=2)[CH:5]=[N:4][CH:3]=[N:2]1.CCN(CC)CC.[CH3:29][N:30]([CH3:35])[S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl>[CH3:29][N:30]([CH3:35])[S:31](=[O:33])(=[O:32])[O:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]2[CH:12]=[C:7]([CH2:6][N:1]3[CH:5]=[N:4][CH:3]=[N:2]3)[CH:8]=[CH:9][C:10]=2[C:20]#[N:21])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 235857225-((1H-1,2,4-triazol-1-yl)methyl)-4'-hydroxybiphenyl-2-carbonitrile

Product 1

HCID 451409545'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl dimethylsulfamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a white suspension of 19 (0.075 g, 0.271 mmol) and NEt3 (0.292 mL, 2.71 mmol) in anhydrous CH2Cl2 (2 mL) at 0° C. under an inert atmosphere was added to a colourless solution of N,N-dimethylsulfamoyl chloride (0.408 mL, 3.80 mmol) in anhydrous CHACl2 (3 mL). The resulting white suspension was left to stir under an inert atmosphere at room temperature for 70 h forming a clear orange/brown solution. The reaction mixture was diluted in CH2Cl2 (30 mL) and washed with distilled H2O (30 mL×3) and brine (30 mL). The organic fraction was separated, dried (MgSO4), filtered and solvent removed in vacuo to leave yellow residues. Column chromatography (CH2Cl2/acetone 75:25) eluted 21 as a viscous yellow oil (0.093 g, 90%); 1H NMR δH (270 MHz, CDCl3) 3.00 (s, 6H), 5.44 (s, 2H), 7.28-7.33 (m, 2H), 7.39 (d, J=8.7 Hz, 2H), 7.53 (d, J=8.7 Hz, 2H), 7.76 (d, J=7.9 Hz, 1H), 8.00 (s, 1H) and 8.18 (s, 1H); LCMS (APCI−) m/z (rel intensity) 382 (100, [M−H]+; HRMS (ES+) m/z calcd. for C18H18N5O3S [M+H]+: 384.1125, found 384.1143.

Workup

  1. waitThe resulting white suspension was left
  2. customforming a clear orange/brown solution
  3. washwashed with distilled H2O (30 mL×3) and brine (30 mL)
  4. customThe organic fraction was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customsolvent removed in vacuo
  8. customto leave yellow residues
  9. washColumn chromatography (CH2Cl2/acetone 75:25) eluted 21 as a viscous yellow oil (0.093 g, 90%)

Sources & evidence

ORD record
ord-20cef5a05a8948d9a2f959b1286ff399
Source dataset
uspto-grants-2012_01
Patent number
US08093279B2

Reaction notes

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