Potassium Carbonate → HCID 54291266, compound

HRID 396574Notes

Reaction equation

HRID 396574 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[NH:14][S:15]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)(=[O:17])=[O:16])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][C:34]([C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)=[O:35]>Cl>[CH2:1]([O:3][C:4](=[O:25])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[N:14]([CH2:33][C:34]([C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)=[O:35])[S:15]([C:18]1[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=1)(=[O:16])=[O:17])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68303p-Chlorophenacyl bromideHCID 53985536HCID 53985536, compound

Product 1

HCID 54291266HCID 54291266, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 3-[4-chloro-2-(toluene-4-sulfonylamino)-phenyl]-acrylic acid ethyl ester (3.00 g, 7.90 mmol) in NN-dimethylacetamide (15.0 ml) was added potassium carbonate (2.18 g, 15.8 mmol) and 2-bromo-4′-chloroacetophenone (2.03 g, 8.69 mmol). The reaction was stirred for 30 minutes, poured into 1N hydrochloric acid (30 ml) and extracted with methyl f-butyl ether (2×30 ml). The organic extracts were dried over magnesium sulfate, filtered, concentrated to a low volume. Hexanes was added and a solid precipitated. The precipitate was filtered to provide 3-{4-chloro-2-[[2-(4-chloro-phenyl)-2-oxo-ethyl]-(toluene-4-sulfonyl)-amino]-phenyl}-acrylic acid ethyl ester (3.19 g, 76%). mp=162-165° C. 1H NMR (300 MHz, CDCl3) d 1.38 (t, 3, J=7.2), 2.47 (s, 3), 4.28 (q, 2, J=7.2), 5.00 (bs, 2), 6.23 (d, 1, J=16.0), 7.29-7.36 (m, 4), 7.47 (d, 2, J=8.7), 7.54 (d, 1, J=8.4), 7.59 (d, 2, J=8.3), 7.74 (d, 1, J=16.0), 7.88 (d, 2, J=8.7). 13C NMR (75 MHz, CDCl3) d 14.33, 21.62, 57.72, 60.66, 112.49, 120.69, 128.07, 129.21, 129.58, 129.70, 131.22, 132.80, 133.83, 134.80, 135.84, 138.55, 139.28, 140.38, 144.46, 166.02, 191.70. IR 1720, 1698, 1590, 1338, 1313, 1179, 1161, 1089 cm−1. Analysis calculated for C26H23Cl2NO5S: C, 58.65; H, 4.35; N, 2.63. Found: C, 58.74; H, 4.56; N, 2.72.

Workup

  1. extractionextracted with methyl f-butyl ether (2×30 ml)
  2. dry with materialThe organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to a low volume
  5. additionHexanes was added
  6. customa solid precipitated
  7. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-0f16905eb89944469415e0b10b4cac85
Source dataset
uspto-grants-2003_08
Patent number
US06608070B1

Reaction notes

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