Pyridine → HCID 178446856, compound

HRID 1287395Notes

Reaction equation

HRID 1287395 reaction equation
C(Cl)(Cl)=O.[CH3:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:13]1([N:19](C)[C:20](Cl)=[O:21])C=[CH:17][CH:16]=[CH:15][CH:14]=1.[N:24]1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:5][N:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:20]([NH:19][C:13](=[NH:24])[CH2:14][CH2:15][CH2:16][CH3:17])=[O:21]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6371PhosgeneHCID 7515N-MethylanilineHCID 77969Carbamic chloride, N-methyl-N-phenyl-

Product 1

HCID 178446856HCID 178446856, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 29.4 g. phosgene in 350 ml. dry chloroform at 5°C. was added a solution of 32.1 g. N-methylaniline and 23.7 g. dry pyridine in 80 ml. dry chloroform dropwise during 45 minutes and the resulting solution was allowed to stand at 5°C. for 3 hours. The solution was evaporated to dryness under reduced pressure and the resulting residue was dissolved in ether. The ethereal solution was heated with magnesium sulfate, filtered, the filtrate was evaporated to dryness under reduced pressure and the resulting solid was slurried in n-hexane and filtered to give 31.5 g. N-phenyl- N-methylcarbamyl chloride; m.p. 90°-91°C.

Workup

  1. customThe solution was evaporated to dryness under reduced pressure
  2. dissolutionthe resulting residue was dissolved in ether
  3. temperatureThe ethereal solution was heated with magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate was evaporated to dryness under reduced pressure
  6. filtrationfiltered
  7. customto give 31.5 g

Sources & evidence

ORD record
ord-8343e76d981e43b3a38e9410796caf81
Source dataset
uspto-grants-1976_10
Patent number
US03984467

Reaction notes

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