Pyridine → HCID 20402718, compound

HRID 544106Notes

Reaction equation

HRID 544106 reaction equation
[CH3:1][O:2][C:3]([CH:5]([NH:7][C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]([CH2:15][C:16](=[O:26])[NH:17][C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=2)[C:9]=1[CH3:27])[CH3:6])=[O:4].N1C=CC=CC=1.[CH3:34][O:35][CH2:36][C:37](Cl)=[O:38]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([CH:5]([N:7]([C:37](=[O:38])[CH2:36][O:35][CH3:34])[C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]([CH2:15][C:16](=[O:26])[NH:17][C:18]2[CH:19]=[C:20]([Cl:25])[CH:21]=[C:22]([Cl:24])[CH:23]=2)[C:9]=1[CH3:27])[CH3:6])=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 96623Methoxyacetyl chlorideHCID 20402721HCID 20402721, compound

Product 1

HCID 20402718HCID 20402718, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

16.2 g of N-(1'-methoxycarbonyl-ethyl)-2,6-dimethyl-3-(3',5'-dichlorophenylcarbamoylmethyl)-aniline and 3.2 g of pyridine were placed into 120 ml of toluene; and within 15 minutes were added 4.7 g of methoxyacetic acid chloride, dissolved in 30 ml of toluene. After the exothermic reaction had subsided, stirring was maintained for 4 hours at room temperature, and the reaction suspension was then filtered with suction. The yellow filtrate was washed with water, dried over sodium sulfate, and concentrated in a rotary evaporator. The solid residue was digested with ether, and the white crystals were filtered off with suction; m.p. 126°-128° C.

Workup

  1. customAfter the exothermic reaction
  2. filtrationthe reaction suspension was then filtered with suction
  3. washThe yellow filtrate was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in a rotary evaporator
  6. filtrationthe white crystals were filtered off with suction

Sources & evidence

ORD record
ord-01c5f72c75b247beb5828f7564b17b75
Source dataset
uspto-grants-1984_05
Patent number
US04448773

Reaction notes

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