HCID 14230922, compound → HCID 14230923, compound

HRID 3779Notes

Reaction equation

HRID 3779 reaction equation
[CH2:1]([O:3][C:4](=[S:26])[NH:5][NH:6][C:7](=O)[CH:8]([O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)[CH3:9])[CH3:2]>S(=O)(=O)(O)O>[CH2:1]([O:3][C:4]1[S:26][C:7]([CH:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[CH3:9])=[N:6][N:5]=1)[CH3:2]

Participants

3

Reactant 1

HCID 14230922HCID 14230922, compound

Product 1

HCID 14230923HCID 14230923, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To 10 ml of concentrated sulfuric acid cooled to -5° C. was added, with stirring, 2.0 g of 3-[2-[4-(4-chlorophenoxy)phenoxy]-propionyl]-thiocarbazic acid-O-ethyl ester gradually. After stirring at the same temperature for 10 minutes, the reaction mixture was poured over 100 g of ice followed by extracting with ethyl acetate. The resulting ethyl acetate layer was washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by chromatography on silica gel to obtain 1.0 g of the compound No. 7 described in Table 1.

Workup

  1. additionwas added
  2. stirringAfter stirring at the same temperature for 10 minutes
  3. extractionby extracting with ethyl acetate
  4. washThe resulting ethyl acetate layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-38fb1d06294f4f07968ae0a46176877a
Source dataset
uspto-grants-1988_02
Patent number
US04722934

Reaction notes

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