Methanol → HCID 54314131, compound

HRID 1863071Notes

Reaction equation

HRID 1863071 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:17]=[C:16]([CH:18]=O)[CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=1.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[O:29][C:30]3[CH:36]=[C:35]([CH2:37]P(OCC)(OCC)=O)[CH:34]=[CH:33][C:31]=3[N:32]=2)=[CH:24][CH:23]=1.CO>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:17]=[C:16]([CH:18]=[CH:37][C:35]4[CH:34]=[CH:33][C:31]5[N:32]=[C:28]([C:25]6[CH:26]=[CH:27][C:22]([O:21][CH3:20])=[CH:23][CH:24]=6)[O:29][C:30]=5[CH:36]=4)[CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 15062118HCID 15062118, compoundHCID 53666658HCID 53666658, compound

Product 1

HCID 54314131HCID 54314131, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5.06 g (0.02 Mole) of 2-p-methoxyphenyl-6-formylbenzoxazole of the formula ##STR33## (melting point: 161.5°-162.5° C.) and 7.50 g (0.02 mole) of 2-(p-methoxyphenyl)-6-(diethylphosphonomethyl)-benzoxazole of the formula ##STR34## (melting point: 85°-88° C.) in 150 ml of dimethyl formamide is heated to 50° C. and 2.1 g of sodium tert.butylate are added in small amounts to the solution over the course of 15 minutes. The reaction mixture is stirred at room temperature overnight, then poured into 400 ml of methanol with stirring. The product is collected by filtration, washed with water and then with 140 ml of methanol, and subsequently recrystallised from chlorobenzene with the addition of fuller's earth, affording 7.1 g (75% of theory) of 1,2-bis-(2-p-methoxyphenyl-benzoxazol-6-yl)-ethylene of the formula ##STR35## in the form of pale yellow crystals with a melting point of over 300° C.

Workup

  1. stirringwith stirring
  2. filtrationThe product is collected by filtration
  3. washwashed with water
  4. customwith 140 ml of methanol, and subsequently recrystallised from chlorobenzene with the addition of fuller's earth

Sources & evidence

ORD record
ord-405e5902401649c38ef533312bb10dd3
Source dataset
uspto-grants-1979_09
Patent number
US04167628

Reaction notes

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