Pyridine → HCID 20352749, compound

HRID 371989Notes

Reaction equation

HRID 371989 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:11]([CH3:19])[CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[O:10])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:26](Cl)(=[O:28])[CH3:27]>O>[C:26]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:11]([CH3:19])[CH2:12][C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)=[O:10])=[CH:4][CH:3]=1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 20352827HCID 20352827, compound

Product 1

HCID 20352749HCID 20352749, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a chilled (circa 0° C.) solution of 5.12 gms. (0.02 mole) of 1-(p-aminophenyl)-3-methyl-3-(4-pyridylmethyl)urea (Example 6., supra.) in 75 ml. of pyridine there is added dropwise 1.48 gms. (0.02 mole) of acetyl chloride with stirring, while maintaining the temperature of the reaction mixture at circa 0° C. Stirring is continued for 30 minutes and then the reaction mixture is allowed to stand at room temperature overnight. Solvent is stripped and the residue suspended in water. Upon removal of the water there is obtained 1-(p-acetamidophenyl)-3-methyl-3-(4-pyridylmethyl)urea.

Workup

  1. temperatureTo a chilled (circa 0° C.) solution of 5.12 gms
  2. temperaturewhile maintaining the temperature of the reaction mixture at circa 0° C
  3. waitto stand at room temperature overnight
  4. customUpon removal of the water

Sources & evidence

ORD record
ord-a1f0c9d2a6e04a3ba75b4a0b76280305
Source dataset
uspto-grants-1978_05
Patent number
US04088766

Reaction notes

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