Triethylamine → HCID 18348345, compound

HRID 2268004Notes

Reaction equation

HRID 2268004 reaction equation
[CH2:1]([N:3]1[C:7]([OH:8])=[C:6]([C:9]([C:11]2[CH:12]=[CH:13][C:14]3[S:19](=[O:21])(=[O:20])[CH2:18][CH2:17][S:16](=[O:23])(=[O:22])[C:15]=3[C:24]=2[CH3:25])=[O:10])[CH:5]=[N:4]1)[CH3:2].[C:26](Cl)(=[O:30])[CH2:27][CH2:28][CH3:29].C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([N:3]1[C:7]([O:8][C:26]([CH2:27][CH2:28][CH3:29])=[O:30])=[C:6]([C:9]([C:11]2[CH:12]=[CH:13][C:14]3[S:19](=[O:21])(=[O:20])[CH2:18][CH2:17][S:16](=[O:23])(=[O:22])[C:15]=3[C:24]=2[CH3:25])=[O:10])[CH:5]=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 178463101HCID 178463101, compound

Product 1

HCID 18348345HCID 18348345, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

1.5 g (3.9 mmol) of 1-ethyl-5-hydroxy-4-(8-methyl-2,3-dihydro-1,1,4,4-tetraoxobenz[1,4]dithiin-7-yl)carbonylpyrazole were suspended in 20 ml of methylene chloride, and 0.42 g (3.9 mmol) of butyryl chloride and 0.39 g (0.42 mol) of triethylamine were added. After five hours of stirring at 20° C., the mixture was washed with 2N hydrochloric acid, sodium bicarbonate solution and water, dried and filtered off, and the solvent was distilled off. The residue was subsequently chromatographed over silica gel (mobile phase: ethyl acetate/cyclohexane=2/3).

Workup

  1. washthe mixture was washed with 2N hydrochloric acid, sodium bicarbonate solution and water
  2. customdried
  3. filtrationfiltered off
  4. distillationthe solvent was distilled off
  5. customThe residue was subsequently chromatographed over silica gel (mobile phase: ethyl acetate/cyclohexane=2/3)

Sources & evidence

ORD record
ord-52057da94476481d85af72206603405d
Source dataset
uspto-grants-2001_12
Patent number
US06326333B1

Reaction notes

Loading…