4-Chloroaniline → HCID 54513953, compound

HRID 848671Notes

Reaction equation

HRID 848671 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH3:12])[N:7]=[C:6]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][CH:14]=2)[N:5]=1)[CH3:2].ClC1C=CC(N)=CC=1.[CH3:29][C:30]1[CH:31]=[CH:32][C:33]2[O:37][C:36]([C:38]3[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=3)=[N:35][C:34]=2[CH:45]=1.[OH-].[K+]>CN(C)C=O.CO.O>[CH3:29][C:30]1[CH:31]=[CH:32][C:33]2[O:37][C:36]([C:38]3[CH:43]=[CH:42][C:41]([CH:44]=[CH:19][C:16]4[CH:15]=[CH:14][C:13]([C:6]5[N:7]=[C:8]([O:10][CH2:11][CH3:12])[CH:9]=[C:4]([O:3][CH2:1][CH3:2])[N:5]=5)=[CH:18][CH:17]=4)=[CH:40][CH:39]=3)=[N:35][C:34]=2[CH:45]=1

Participants

8

Reactant 4

HCID 78124-ChloroanilineHCID 14797Potassium HydroxideHCID 85307Benzoxazole, 5-methyl-2-(4-methylphenyl)-HCID 127037284-(4,6-Diethoxy-2-pyrimidinyl)benzaldehyde

Product 1

HCID 54513953HCID 54513953, compoundYield 55.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

3.82 g of the Schiff's base of the formula ##STR77## which is obtained from 4,6-diethoxy-2-(p-formylphenyl)-pyrimidine and p-chloroaniline and has a melting point of 129.5°-130° C., 2.23 g of 5-methyl-2-(p-tolyl)-benzoxazole of the formula ##STR78## and 3.75 g of potassium hydroxide powder with a water content of about 10% are stirred in 80 ml of dimethylformamide under nitrogen. The reaction mixture is warmed to 60° C. in the course of 15 minutes and is stirred for a further one hour at 60°-65° C. After adding 400 ml of methanol, the mixture is cooled to -10° C. and the product which has precipitated is filtered off with suction, washed with 100 ml of methanol and dried. 2.64 g (55.3% of theory) of 2-[4'-(5-methyl-benzoxazol-2-yl)-stilben-4-yl]-4,6-diethoxy-pyrimidine of the formula ##STR79## are obtained in the form of a pale yellow powder with a melting point of 233°-234° C. After twice recrystallising from toluene, and with the aid of bleaching earth, 2.12 g (44.4% of theory) of small, pale greenish-tinged yellow, matted needles are obtained, which melt at 236°-237° C.

Workup

  1. temperaturethe mixture is cooled to -10° C.
  2. customthe product which has precipitated
  3. filtrationis filtered off with suction
  4. washwashed with 100 ml of methanol
  5. customdried

Sources & evidence

ORD record
ord-1a0d43da4f87437b8ef6aa2d4ce813c9
Source dataset
uspto-grants-1981_10
Patent number
US04297234

Reaction notes

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