Acetic Acid → HCID 87734300, compound

HRID 2253251Notes

Reaction equation

HRID 2253251 reaction equation
[Cl:1][C:2]1[CH:43]=[C:42]([Cl:44])[CH:41]=[CH:40][C:3]=1[CH2:4][O:5][C@H:6]1[C@H:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[C@@H:17]([CH2:29][O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=2[Cl:39])[S:16][CH:7]1SCC1C=CC=CC=1.[C:45]([OH:48])(=[O:47])[CH3:46]>C(Cl)Cl>[Cl:1][C:2]1[CH:43]=[C:42]([Cl:44])[CH:41]=[CH:40][C:3]=1[CH2:4][O:5][C@H:6]1[C@H:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[C@@H:17]([CH2:29][O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=2[Cl:39])[S:16][CH:7]1[O:47][C:45](=[O:48])[CH3:46]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 87735156HCID 87735156, compound

Product 1

HCID 87734300HCID 87734300, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of mercuric acetate in acetic acid is added compound 1-4 from Step D and the resulting reaction mixture is stirred at room temperature for 2-3 h. The mixture is then diluted with CH2Cl2, washed with water, saturated aqueous sodium bicarbonate and 5% KCN solution. The organic layer is dried over anhydrous sodium sulfate, filtered, and evaporated. The residue is purified on a silica gel column using a mixture of cyclohexane and ethyl acetate as eluent. The appropriate fractions are combined and concentrated to give the title compound 1-5.

Workup

  1. customthe resulting reaction mixture
  2. washwashed with water, saturated aqueous sodium bicarbonate and 5% KCN solution
  3. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified on a silica gel column
  7. additiona mixture of cyclohexane and ethyl acetate as eluent
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-801ab21a8c7c4f82b3013a27b73f6868
Source dataset
uspto-grants-2008_01
Patent number
US07323449B2

Reaction notes

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