Water → HCID 15382033, compound

HRID 744090Notes

Reaction equation

HRID 744090 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:10][C:11]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[S:12])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:34][O:35][C:36]1[CH:37]=[C:38]([CH:42]=[C:43]([O:47][CH3:48])[C:44]=1[O:45][CH3:46])[C:39](Cl)=[O:40].O>C(Cl)Cl>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[CH:10][C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:39](=[O:40])[C:38]3[CH:37]=[C:36]([O:35][CH3:34])[C:44]([O:45][CH3:46])=[C:43]([O:47][CH3:48])[CH:42]=3)[CH2:15][CH2:14]2)=[S:12])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 19421602HCID 19421602, compound

Product 1

HCID 15382033HCID 15382033, compoundYield 357.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.049 g of 1-[3,3-bis(4-methoxyphenyl)thioacryloyl]piperazine [prepared as described in step (b) above] and 0.29 ml of triethylamine were dissolved in 30 ml of methylene chloride, and 0.157 g of 3,4,5-trimethoxybenzoyl chloride were added, whilst ice-cooling, to the resulting solution. The reaction mixture was then stirred for 1 hour at room temperature, after which it was poured into water and extracted twice with methylene chloride. The combined extracts were washed with 10% w/v aqueous hydrochloric acid, with a saturated aqueous solution of sodium bicarbonate and with water, in that order, after which they were dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography through 40 g of silica gel and by medium pressure liquid chromatography using a Lobar B column using mixtures of methylene chloride and ethyl acetate ranging from 9:1 to 4:1 by volume as eluent, to give 1.368 g of the title compound as a yellow powder.

Workup

  1. temperaturecooling, to the resulting solution
  2. extractionextracted twice with methylene chloride
  3. washThe combined extracts were washed with 10% w/v aqueous hydrochloric acid, with a saturated aqueous solution of sodium bicarbonate and with water, in that order
  4. dry with materialafter which they were dried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography through 40 g of silica gel and by medium pressure liquid chromatography

Sources & evidence

ORD record
ord-1d77b78af30043cd897ddf1fd5e56aa6
Source dataset
uspto-grants-1996_09
Patent number
US05559109

Reaction notes

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