Water → 5-Chloro-2-{4-[2-(2-phenyl-1,3-benzoxazol-6-yl)ethenyl]phenyl}-1,3-benzoxazole

HRID 1863070Notes

Reaction equation

HRID 1863070 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[CH:15]=[C:14]([CH:16]=O)[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OP([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[O:34][C:35]3[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][C:36]=3[N:37]=2)=[CH:29][CH:28]=1)(OCC)=O)C.O>CN(C)C=O>[C:1]1([C:7]2[O:8][C:9]3[CH:15]=[C:14]([CH:16]=[CH:26][C:27]4[CH:28]=[CH:29][C:30]([C:33]5[O:34][C:35]6[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][C:36]=6[N:37]=5)=[CH:31][CH:32]=4)[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 127037382-Phenyl-1,3-benzoxazole-6-carbaldehydeHCID 20393280HCID 20393280, compound

Product 1

HCID 543750725-Chloro-2-{4-[2-(2-phenyl-1,3-benzoxazol-6-yl)ethenyl]phenyl}-1,3-benzoxazoleYield 33.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4.46 g (0.02 mole) of 2-phenyl-6-formyl-benzoxazole of the formula ##STR29## (melting point: 133°-135° C.) and 7.59 g (0.02 mole) of 2-(p-diethylphosphonomethylphenyl)-5-chloro-benzoxazole of the formula ##STR30## (melting point: 96°-98°) in 80 ml of dimethyl formamide is heated to 40° C. Then 2.1 g (0.022 mole) of sodium tert.butylate are added in small amounts to the solution over the course of 30 minutes and the resultant suspension is further stirred for 4 hours at 40° C. The reaction mixture is poured into water and the precipitate is collected by filtration, washed with water and subsequently with a total amount of 110 ml of methanol. The product is recrystallised form a solvent mixture of nonane/xylene (1:1) with the addition of fuller's earth, affording 3 g (30% of theory) of 1-(2-phenylbenzoxazol-6-yl)-2-[4'-(5-chlorbenzoxazol-2-yl)-phenyl]-ethylene of the formula ##STR31## in the form of pale yellow flakes having a melting point of 241°-242° C.

Workup

  1. filtrationthe precipitate is collected by filtration
  2. washwashed with water and subsequently with a total amount of 110 ml of methanol
  3. customThe product is recrystallised form
  4. additiona solvent mixture of nonane/xylene (1:1)
  5. additionwith the addition of fuller's earth

Sources & evidence

ORD record
ord-bb8e12a7723e43c28cd7bfdfa60ca308
Source dataset
uspto-grants-1979_09
Patent number
US04167628

Reaction notes

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