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Benzoyl chloride → HCID 13318174, compound

HRID 1262816
Notes
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Reaction equation

HRID 1262816 reaction equation
[CH3:1][C:2]1[C:6]([OH:7])=[C:5]([C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])[S:4][C:3]=1[C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15].C(N(CC)CC)C.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O1CCOCC1>[CH3:1][C:2]1[C:6]([O:7][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:5]([C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])[S:4][C:3]=1[C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 54703303HCID 54703303, compound

Product 1

HCID 13318174HCID 13318174, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of di-isopropyl 3-methyl-4-hydroxy-2,5-thiophene-dicarboxylate (656 g, 2.30 mol), triethylamine (297 g, 2.98 mol) and dioxane (2 l) was cooled with ice to about 10° C. The solution was added, while stirring, with benzoyl chloride (351 g, 2.5 mol) over about 10 minutes, followed by further stirring for 30 minutes at room temperature. After removing the precipitate of triethylamine hydrochloride salt by filtration, the solution was distilled in vacuo to remove dioxane. Toluene was then added to the remaining residue, and the solution was washed with 5% aqueous sodium bicarbonate and water, and then dried over MgSO4. The solvent was removed by distillation to give almost pure di-isopropyl 3-methyl-4-benzoyloxy-2,5-thiophene dicarboxylate (851 g, 95%). nD10 1.5499.

Workup

  1. additionThe solution was added
  2. customAfter removing the precipitate of triethylamine hydrochloride salt
  3. filtrationby filtration
  4. distillationthe solution was distilled in vacuo
  5. customto remove dioxane
  6. additionToluene was then added to the remaining residue
  7. washthe solution was washed with 5% aqueous sodium bicarbonate and water
  8. dry with materialdried over MgSO4
  9. customThe solvent was removed by distillation

Sources & evidence

ORD record
ord-ce623c9f9d4e478eb4717369f83e9235
Source dataset
uspto-grants-1984_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04454131

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes