2-Thiophenecarbonyl chloride → HCID 13532781, compound

HRID 1906263Notes

Reaction equation

HRID 1906263 reaction equation
[OH:1][CH2:2][N:3]1[C:8](=[O:9])[CH2:7][N:6]([CH2:10][CH2:11][N:12]2[CH2:17][C:16](=[O:18])[N:15]([CH2:19][OH:20])[C:14](=[O:21])[CH2:13]2)[CH2:5][C:4]1=[O:22].[C:23]1([C:28](Cl)=[O:29])[S:27][CH:26]=[CH:25][CH:24]=1>N1C=CC=CC=1>[C:23]1([C:28]([O:20][CH2:19][N:15]2[C:14](=[O:21])[CH2:13][N:12]([CH2:11][CH2:10][N:6]3[CH2:7][C:8](=[O:9])[N:3]([CH2:2][O:1][C:28](=[O:29])[C:23]4[S:27][CH:26]=[CH:25][CH:24]=4)[C:4](=[O:22])[CH2:5]3)[CH2:17][C:16]2=[O:18])=[O:29])[S:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 789282-Thiophenecarbonyl chlorideHCID 13532751HCID 13532751, compound

Product 1

HCID 13532781HCID 13532781, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 1,2-bis(4-hydroxymethyl-3,5-dioxopiperazin-1-yl)ethane (6.30 g, 22 m mol) and pyridine (60 ml), thenoyl chloride (6.45 g, 44 m mol) was added gradually at 0° C., and then the mixture was stirred for 4 hours at room temperature. The solvent was removed from the reaction mixture under reduced pressure, and the residue was extracted with chloroform. The extract solution was washed with 10% sulfuric acid solution and successively with water, and was dried over magnesium sulfate. The residue obtained by removing the solvent from the extract solution under reduced pressure was purified by silica gel column chromatography (ethyl acetate, Rf value=0.6) to give the titled compound (8.20 g; yield 70%).

Workup

  1. additionwas added gradually at 0° C.
  2. customThe solvent was removed from the reaction mixture under reduced pressure
  3. extractionthe residue was extracted with chloroform
  4. washThe extract solution was washed with 10% sulfuric acid solution and successively with water
  5. dry with materialwas dried over magnesium sulfate
  6. customThe residue obtained
  7. customby removing the solvent from the extract solution under reduced pressure
  8. customwas purified by silica gel column chromatography (ethyl acetate, Rf value=0.6)

Sources & evidence

ORD record
ord-c986b45709c54c389dae100483c671f3
Source dataset
uspto-grants-1987_03
Patent number
US04650799

Reaction notes

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