Phosphorus oxychloride → HCID 86608145, compound

HRID 1094997Notes

Reaction equation

HRID 1094997 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([O:8][C:9]([C:11]1[C:15]([CH3:16])=[CH:14][S:13][C:12]=1[NH:17][C:18](=[O:31])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[CH:20]=1)=[O:10])[CH3:7].[C:32](=O)([O-])[OH:33].[Na+]>CN(C)C=O>[CH2:6]([O:8][C:9]([C:11]1[C:15]([CH3:16])=[C:14]([CH:32]=[O:33])[S:13][C:12]=1[NH:17][C:18](=[O:31])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[CH:20]=1)=[O:10])[CH3:7]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 66637729HCID 66637729, compound

Product 1

HCID 86608145HCID 86608145, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Separately, phosphorus oxychloride (200 μl) was added dropwise to N,N-dimethylformamide (73 mg) at 0° C., and the mixture was stirred at that temperature for 5 min. The reaction system was heated to 80° C., 2-(3-diethylaminomethyl-benzoylamino)-4-methyl-thiophene-3-carboxylic acid ethyl ester (187 mg) synthesized by the above process was then added thereto, and the mixture was stirred at that temperature for 3 hr. After the completion of the reaction, the reaction solution was neutralized with a saturated sodium hydrogencarbonate solution, and was then subjected to separatory extraction with chloroform, and the organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-(3-diethylaminomethyl-benzoylamino)-5-formyl-4-methylthiophene-3-carboxylic acid ethyl ester as a useful intermediate (110 mg, yield 53%).

Workup

  1. additionwas then added
  2. stirringthe mixture was stirred at that temperature for 3 hr
  3. customAfter the completion of the reaction
  4. extractionwas then subjected to separatory extraction with chloroform
  5. washthe organic layer was washed with saturated brine
  6. dry with materialwas dried over sodium sulfate
  7. concentrationwas then concentrated under the reduced pressure
  8. customThe residue was purified by column chromatography
  9. washeluted with a chloroform-methanol system

Sources & evidence

ORD record
ord-d92ecd1698ad4113a3dd3da642461002
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

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