Water → HCID 57069684, compound

HRID 2231977Notes

Reaction equation

HRID 2231977 reaction equation
[Cl:1][C:2]1[N:9]=[C:8](Cl)[CH:7]=[C:6]([CH3:11])[C:3]=1[C:4]#[N:5].NCCNC(=O)[CH:17]([C:19]1[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:22]([OH:29])=[C:21]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:20]=1)[CH3:18].C([N:37](CC)CC)C.O.C[N:44]1[CH2:48][CH2:47]C[C:45]1=[O:49]>C1(C)C=CC=CC=1>[C:30]([C:21]1[CH:20]=[C:19]([CH2:17][CH2:18][C:45]([NH:44][CH2:48][CH2:47][NH:37][C:8]2[CH:7]=[C:6]([CH3:11])[C:3]([C:4]#[N:5])=[C:2]([Cl:1])[N:9]=2)=[O:49])[CH:24]=[C:23]([C:25]([CH3:28])([CH3:26])[CH3:27])[C:22]=1[OH:29])([CH3:33])([CH3:32])[CH3:31]

Participants

7

Reactant 5

HCID 962WaterHCID 8471TriethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 701313-Cyano-2,6-dichloro-4-methylpyridineHCID 22104623HCID 22104623, compound

Product 1

HCID 57069684HCID 57069684, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

18.7 g of 2,6-dichloro-4-methylnicotinonitrile and 32 g of 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid 2-aminoethylamide are reacted with 10.1 g of triethylamine in 0.2 l of N-methylpyrrolidone at 50° C. for 8 hours, after which 1 l of water and 0.4 l of toluene are added, the toluene phase is separated off, dried and filtered over active carbon, and the filtrate is evaporated down. The residue is dissolved in 100 ml of hot ethanol, and 1 l of petroleum ether is slowly added to the solution. The mixture is cooled, and the precipitate is filtered off under suction and dried to give a product of melting point 162°-165° C.

Workup

  1. customthe toluene phase is separated off
  2. customdried
  3. filtrationfiltered over active carbon
  4. customthe filtrate is evaporated down
  5. dissolutionThe residue is dissolved in 100 ml of hot ethanol
  6. addition1 l of petroleum ether is slowly added to the solution
  7. temperatureThe mixture is cooled
  8. filtrationthe precipitate is filtered off under suction
  9. customdried
  10. customto give a product of melting point 162°-165° C.

Sources & evidence

ORD record
ord-23c2844a1e964804a3e1820609c83d29
Source dataset
uspto-grants-1988_11
Patent number
US04785107

Reaction notes

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