Diisopropylethylamine → HCID 10924839, compound

HRID 1398280Notes

Reaction equation

HRID 1398280 reaction equation
[C:1]([OH:7])(=[O:6])/[C:2](=[CH:4]\[CH3:5])/[CH3:3].C(N(C(C)C)CC)(C)C.[Cl:17][C:18]1[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[C:19]=1[C:20](Cl)=[O:21]>ClCCl>[CH3:3]/[C:2](=[CH:4]/[CH3:5])/[C:1]([O:7][C:20](=[O:21])[C:19]1[C:23]([Cl:28])=[CH:24][C:25]([Cl:27])=[CH:26][C:18]=1[Cl:17])=[O:6]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6439152,3-Dimethylacrylic acid, (Z)-HCID 27337032,4,6-Trichlorobenzoyl chloride

Product 1

HCID 10924839HCID 10924839, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2 °C

Procedure

Angelic acid (601 mg, 6.0 mmol) was dissolved in dichloromethane (3.0 mL) under argon. Diisopropylethylamine (1.23 mL, 7.20 mmol) was added at 5-10° C. in a period of 1 min. To this solution was added 2,4,6-trichlorobenzoyl chloride (1.12 mL, 7.20 mmol) at 3-6° C. in a period of 4 min. After the reaction solution had been stirred at 2° C. for 45 min, petroleum ether (9.0 mL) was added. The obtained suspension was purified by flash chromatography (petroleum ether/dichloromethane 3:1), giving the title compound as a white solid (605 mg, 33%).

Workup

  1. customThe obtained suspension was purified by flash chromatography (petroleum ether/dichloromethane 3:1)

Sources & evidence

ORD record
ord-d664243ed8d84e8ca51746c237f6fc43
Source dataset
uspto-grants-2014_12
Patent number
US08901356B2

Reaction notes

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