Triethylamine → HCID 68461240, compound

HRID 498929Notes

Reaction equation

HRID 498929 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([F:17])[C:14]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[N:20]([CH3:29])[C:19]2=[O:30])=[CH:13][C:3]=1[C:4]([O:6][C:7]([CH3:12])([CH3:11])[C:8]([OH:10])=[O:9])=[O:5].[CH3:31][N:32]([CH3:37])[S:33]([NH2:36])(=[O:35])=[O:34].C(N(CC)CC)C>S(Cl)(Cl)=O.CN(C)C1C=CN=CC=1.ClCCl>[CH3:31][N:32]([CH3:37])[S:33]([NH2:36])(=[O:35])=[O:34].[Cl:1][C:2]1[CH:16]=[C:15]([F:17])[C:14]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:26])([F:28])[F:27])[N:20]([CH3:29])[C:19]2=[O:30])=[CH:13][C:3]=1[C:4]([O:6][C:7]([CH3:12])([CH3:11])[C:8]([OH:10])=[O:9])=[O:5]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 134472N,N-DimethylsulfamideHCID 17972199HCID 17972199, compound

Product 1

HCID 68461240HCID 68461240, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

0.65 g (1.4 mmol) of 2-[(2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimdin-1-yl)-4-fluorobenzoyloxy]-2-methylpropionic acid from example 4.2 was dissolved in 30 ml of thionyl chloride, the reaction mixture was heated under reflux for 3 hours and the resulting solution of the acid chloride was then concentrated. 0.18 g (1.4 mmol) of N,N-dimethylsulfamide, 0.07 g (1.4 mmol) of 4-dimethylaminopyridine and 0.35 ml (3.5 mmol) of triethylamine were dissolved in 10 ml of dichloromethane, and a solution of the acid chloride which had been prepared beforehand in 10 ml of dichloromethane was then added dropwise. The solution was stirred for 16 hours and then concentrated, and the residue was then dissolved in ethyl acetate. The organic phase was washed with 10% strength hydrochloric acid and water, the organic phase was dried over sodium sulfate, the drying agent was filtered off and the filtrate was concentrated. Column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 2:1) gave 0.30 g of the title compound of melting point 211-213° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 3 hours
  3. concentrationthe resulting solution of the acid chloride was then concentrated
  4. additionwas then added dropwise
  5. concentrationconcentrated
  6. dissolutionthe residue was then dissolved in ethyl acetate
  7. washThe organic phase was washed with 10% strength hydrochloric acid and water
  8. dry with materialthe organic phase was dried over sodium sulfate
  9. filtrationthe drying agent was filtered off
  10. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e5169b58d78e4e5aaa2f648e76bf3736
Source dataset
uspto-grants-2010_08
Patent number
US07767624B2

Reaction notes

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