Chloroform → HCID 86667593, compound

HRID 85304Notes

Reaction equation

HRID 85304 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([NH:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([O:19][CH3:20])[CH:12]=1)[CH2:7][CH2:8][CH3:9].C(Cl)(Cl)Cl.CN(C)[CH:27]=[O:28]>>[CH2:6]([N:10]([CH2:6][CH2:7][CH2:8][CH3:9])[C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([CH:27]=[O:28])=[C:13]([O:19][CH3:20])[CH:12]=1)[CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 4

HCID 6212ChloroformHCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 137939884-Butylamino-2,6-dimethoxybenzene

Product 1

HCID 86667593HCID 86667593, compoundYield 80%

Conditions

Temperature
7.5 °C

Procedure

In a stream of argon, to 30 ml of N,N-dimethylformamide was added 16.0 g (104 mmol) of phosphorus oxychloride under cooling at 5 to 10° C. and stirring. After the mixture was well-stirred, 23.5 g (80.1 mmol) of 4-butylamino-2,6-dimethoxybenzene dissolved in 10 ml of N,N-dimethylformamide was added dropwise. The mixture was reacted with stirring for 1.5 hours. After the mixture was poured into 70 ml of ice water, extraction with 200 ml of chloroform, washing with a saturated saline solution, drying over anhydrous magnesium sulfate, and concentration were performed. The residue was purified by silica gel chromatography to give 18.8 g (yield: 80%) of 4-dibutylamino-2,6-dimethoxybenzaldehyde as a dark purple crystal (mp: 55-56° C.)

Workup

  1. stirringAfter the mixture was well-stirred
  2. additionwas added dropwise
  3. customThe mixture was reacted
  4. stirringwith stirring for 1.5 hours
  5. washwashing with a saturated saline solution
  6. dry with materialdrying over anhydrous magnesium sulfate, and concentration
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-46197a9033de47c596ab244156fbcaf9
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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