Chlorosulfamic acid → 5''-((1H-1,2,4-triazol-1-yl)methyl)-2''-cyanobiphenyl-4-yl sulfamate

HRID 418417Notes

Reaction equation

HRID 418417 reaction equation
[NH2:1][S:2](Cl)(=[O:4])=[O:3].CC(N(C)C)=O.[N:12]1([CH2:17][C:18]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=3)[C:21]([C:31]#[N:32])=[CH:20][CH:19]=2)[CH:16]=[N:15][CH:14]=[N:13]1>CCOC(C)=O>[S:2](=[O:4])(=[O:3])([O:30][C:27]1[CH:28]=[CH:29][C:24]([C:22]2[CH:23]=[C:18]([CH2:17][N:12]3[CH:16]=[N:15][CH:14]=[N:13]3)[CH:19]=[CH:20][C:21]=2[C:31]#[N:32])=[CH:25][CH:26]=1)[NH2:1]

Participants

5

Reactant 3

HCID 24499Chlorosulfamic acidHCID 31374DimethylacetamideHCID 235857225-((1H-1,2,4-triazol-1-yl)methyl)-4'-hydroxybiphenyl-2-carbonitrile

Product 1

HCID 451409535''-((1H-1,2,4-triazol-1-yl)methyl)-2''-cyanobiphenyl-4-yl sulfamate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

As general method using H2NSO2Cl (4.63 mL, 1.39 mmol), DMA (1.5 mL) and 19 (0.077 g, 0.279 mmol). The reaction mixture was poured into EtOAc (30 mL). The organic layer separated was washed with distilled H2O (30 mL×4), brine (30 mL), dried (MgSO4) and evaporated in vacuo to give white residues. Column chromatography (CH2Cl2/acetone 80:20) eluted 15 as a white solid (0.074 g, 75%), mp 159-162° C.; 1H NMR δH (270 MHz, DMSO-d6) 5.60 (s, 2H), 7.41-7.46 (m, 314), 7.51 (s, 1H), 7.67 (d, J=8.2, 2H), 7.98 (d, J=7.9, 1H), 8.03 (s, 1H), 8.17 (br s, 214) and 8.73 (s, 1H);

Workup

  1. customThe organic layer separated
  2. washwas washed with distilled H2O (30 mL×4), brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customto give white residues
  6. washColumn chromatography (CH2Cl2/acetone 80:20) eluted 15 as a white solid (0.074 g, 75%), mp 159-162° C.

Sources & evidence

ORD record
ord-3d99a62170744cc286c5f6a970d9bf68
Source dataset
uspto-grants-2012_01
Patent number
US08093279B2

Reaction notes

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