Water → Sulfamic acid 3-[2-cyano-1-(3,5-dimethoxy-phenyl)-vinyl]-phenyl ester

HRID 2378279Notes

Reaction equation

HRID 2378279 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)=[CH:12][C:13]#[N:14])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[S:22](Cl)(=[O:25])(=[O:24])[NH2:23].C(Cl)Cl.O>CC(N(C)C)=O>[C:13]([CH:12]=[C:11]([C:15]1[CH:16]=[C:17]([O:21][S:22](=[O:25])(=[O:24])[NH2:23])[CH:18]=[CH:19][CH:20]=1)[C:5]1[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)#[N:14]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 24499Chlorosulfamic acidHCID 692024963-(3,5-Dimethoxy-phenyl)-3-(3-hydroxy-phenyl)-acrylonitrile

Product 1

HCID 69203172Sulfamic acid 3-[2-cyano-1-(3,5-dimethoxy-phenyl)-vinyl]-phenyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 3-(3,5-dimethoxy-phenyl)-3-(3-hydroxy-phenyl) -acrylonitrile (280 mg, 1 mmol) in dimethylacetamide (4 mL) was added a solution of sulfamic chloride in methylene chloride (1 mL, 2.3 mmol/mL, 2.3 mmol) at room temperature. After 15 h, water (30 mL) was added to the mixture. The aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic layers was washed with water (50 mL), brine (50 mL) and dried over magnesium sulfate. Removal of solvent and chromatography gave (E/Z) sulfamic acid 3-[2-cyano-1-(3,5-dimethoxy-phenyl)-vinyl]-phenyl ester (320 mg, 89% yield): mp, 301-303° C.; 1H NMR (DMSO-d6) δ 3.73 (s, 6H, 2CH3), [3.76 (s)], [6.41 (s)], 6.44 (s, 1H, CH), 6.49-6.51 (m, 2H, Ar), 6.63-6.67 (m, 1H, Ar), 7.22 (brs, 1H, Ar), 7.38-7.65 (m, 3H, Ar), 8.07 (brs, 2H, NH2); Anal. Calcd for C17H16N2O5S+0.1H2O: C, 56.38; H, 4.51; N, 7.73. Found: C, 56.23; H, 4.36; N, 7.55.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  2. washThe combined organic layers was washed with water (50 mL), brine (50 mL)
  3. dry with materialdried over magnesium sulfate
  4. customRemoval of solvent and chromatography

Sources & evidence

ORD record
ord-42d8c9aa96ec4f9393f6118835295604
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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