Triethylamine → HCID 66801152, compound

HRID 1913313Notes

Reaction equation

HRID 1913313 reaction equation
[Cl:1][C:2]1[S:3][C:4]([Cl:10])=[CH:5][C:6]=1[C:7](O)=[O:8].C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[CH3:24][NH:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1>ClCCl.CN(C)C=O.O>[CH3:24][N:25]([C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)[C:7]([C:6]1[CH:5]=[C:4]([Cl:10])[S:3][C:2]=1[Cl:1])=[O:8]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 140376N-Methyl-3-pyridinamineHCID 2254382,5-Dichlorothiophene-3-carboxylic acid

Product 1

HCID 66801152HCID 66801152, compoundYield 64.6%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

394 mg (2.0 mmol, 1.0 equiv.) of 2,5-dichloro-thiophene-3-carboxylic acid were dissolved in 8 ml of dichloromethane and 254 mg (2.0 mmol, 1.0 equiv.) of oxalyl chloride were added dropwise. A catalytic amount of N,N-dimethylformamide (DMF) (5 drops) was added and the reaction mixture was stirred at room temperature for 4 h. Then, the mixture was added dropwise to a solution of 300 mg (3.0 mmol, 1.5 equiv) of triethylamine and 217 mg (2.0 mmol, 1.0 equiv.) of methyl-pyridin-3-yl-amine in 6 ml of dichloromethane and the reaction was stirred at room temperature overnight. Water was added and the mixture was extracted with dichloromethane. The combined organic phases were dried over Na2SO4, filtered and the solvent was removed under reduced pressure to yield 371 mg of the title compound (65%, 95% purity), [Mt]: 288.1.

Workup

  1. stirringthe reaction was stirred at room temperature overnight
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-62ad0c33544243689ecf81a814f1c5a1
Source dataset
uspto-grants-2013_12
Patent number
US08609700B2

Reaction notes

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