Phenylsulphonyl isocyanate → HCID 69203552, compound

HRID 2378257Notes

Reaction equation

HRID 2378257 reaction equation
[C:1]1([S:7]([N:10]=[C:11]=[O:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:13][C:14]1[CH:15]=[C:16]([C:22]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH2:35][CH3:36])[CH:27]=2)=[CH:23][C:24]#[N:25])[CH:17]=[CH:18][C:19]=1[O:20][CH3:21]>C1COCC1>[C:1]1([S:7]([NH:10][C:11]([NH:13][C:14]2[CH:15]=[C:16]([C:22]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH2:35][CH3:36])[CH:27]=3)=[CH:23][C:24]#[N:25])[CH:17]=[CH:18][C:19]=2[O:20][CH3:21])=[O:12])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 76096Phenylsulphonyl isocyanateHCID 69204282HCID 69204282, compound

Product 1

HCID 69203552HCID 69203552, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzenesulfonyl isocyanate (0.4 mL, 2.6 mmol) was added to a stirred solution of (E/Z) 3-(3-amino-4-methoxy-phenyl)-3-(3-ethoxy-4-methoxy-phenyl)-acrylonitrile (0.70 g, 2.2 mmol) in anhydrous THF (25 mL). The reaction mixture was stirred at room temperature for 2 h. Removal of solvent and chromatography (Silica Gel) gave a mixture of (E/Z) 1-benzenesulfonyl-3-{5-[2-cyano-1-(3-ethoxy-4-methoxy-phenyl)-vinyl]-2-methoxy-phenyl}-urea as a solid (0.66 g, 61% yield): mp, 168-170° C.; 1H NMR (CDCl3) δ 1.38-1.46 (m, 6H, 2CH3), 3.87-4.14 (m, 16H, 4OCH3+2CH2), 5.55-5.58 (2s, 2H, 2CH), 6.78-7.98 (m, 22H, Ar), 8.03-9.06 (m, 4H, 4NH); 13C NMR (CDCl3) δ 14.67, 55.92, 55.97, 56.06, 56.24, 64.53, 92.07, 92.54, 109.82, 109.88, 110.99, 111.07, 112.65, 114.13, 118.58, 118.78, 119.77, 121.04, 122.25, 123.07, 125.52, 125.98, 126.56, 126.80, 127.02, 127.11, 129.35, 129.45, 129.50, 129.87, 131.16, 132.15, 133.96, 134.05, 139.46, 147.88, 148.19, 149.75, 150.25, 150.85, 151.59, 162.14, 162.83; Anal. Calcd for C26H25N3O6S+0.12H2O: C, 61.27; H, 4.99; N, 8.24; S, 6.29. Found: C, 60.90; H, 5.04; N, 8.05; S, 6.28.

Workup

  1. customRemoval of solvent and chromatography (Silica Gel)
  2. customgave

Sources & evidence

ORD record
ord-7594bac18f574c848e3683401e4d9d8e
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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