Dimethylcarbamoyl Chloride → HCID 69202483, compound

HRID 2378258Notes

Reaction equation

HRID 2378258 reaction equation
C(N(CC)C(C)C)(C)C.[NH2:10][C:11]1[CH:12]=[C:13]([C:19]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH2:32][CH3:33])[CH:24]=2)=[CH:20][C:21]#[N:22])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18].[CH3:34][N:35]([CH3:39])[C:36](Cl)=[O:37]>C(Cl)Cl>[C:21]([CH:20]=[C:19]([C:13]1[CH:14]=[CH:15][C:16]([O:17][CH3:18])=[C:11]([NH:10][C:36](=[O:37])[N:35]([CH3:39])[CH3:34])[CH:12]=1)[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH2:32][CH3:33])[CH:24]=1)#[N:22]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 81531DiisopropylethylamineHCID 69204282HCID 69204282, compound

Product 1

HCID 69202483HCID 69202483, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

N,N-diisopropylethylamine (1.5 mL, 8.6 mmol) was added to a mixture of (E/Z) 3-(3-amino-4-methoxy-phenyl)-3-(3-ethoxy-4-methoxy-phenyl)-acrylonitrile (0.70 g, 2.2 mmol) and dimethylcarbamyl chloride (1.6 mL, 17.3 mmol). The reaction mixture was heated at 85° C. for 3 h. CH2Cl2 (100 ml) was added and the mixture was extracted with water (2×50 mL), 4 N HCl (2×50 mL), water (2×50 mL), saturated NaHCO3 (2×50 mL), brine (50 mL) and dried (MgSO4). Removal of solvent and chromatography (Silica Gel) gave a mixture of (E/Z) 3-{5-[2-cyano-1-(3-ethoxy-4-methoxy-phenyl)-vinyl]-2-methoxy-phenyl}-1,1-dimethyl-urea as a solid (0.59 g, 69% yield): mp, 143-145° C.; 1H NMR (CDCl3) δ 1.40-1.47 (m, 6H, 2CH3), 3.02-3.05 (2s, 12H, 4CH3), 3.88-3.94 (3s, 12H, 4OCH3), 3.99-4.12 (m, 4H, 2CH2), 5.55-5.61 (2s, 2H, 2CH), 6.79-7.18 (m, 12H, Ar), 8.18-8.36 (m, 2H, 2NH); 13C NMR (CDCl3) δ 14.71, 36.33, 55.93, 56.00, 64.46, 92.06, 92.33, 109.21, 109.30, 110.93, 110.99, 112.74, 114.22, 118.56, 118.69, 118.79, 120.27, 122.25, 123.06, 123.41, 123.74, 128.97, 129.24, 129.73, 130.11, 131.68, 132.25, 147.83, 148.14, 148.81, 149.27, 150.68, 151.37, 155.22, 155.31, 162.66, 163.11; Anal. Calcd for C22H25N3O4: C, 66.82; H, 6.37; N, 10.63. Found: C, 66.84; H, 6.48; N, 10.43.

Workup

  1. extractionthe mixture was extracted with water (2×50 mL), 4 N HCl (2×50 mL), water (2×50 mL), saturated NaHCO3 (2×50 mL), brine (50 mL)
  2. dry with materialdried (MgSO4)
  3. customRemoval of solvent and chromatography (Silica Gel)
  4. customgave

Sources & evidence

ORD record
ord-7f80dc9ee6c243f895b0c68c33c34a30
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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