2,2-Dimethyl-3-phenyl-2H-azirene → 4-(2,2-Dimethyl-4-phenyl-2,5-dihydro-1,3-oxazol-5-yl)-N,N,2,6-tetramethylaniline

HRID 2058536Notes

Reaction equation

HRID 2058536 reaction equation
[CH3:1][C:2]1([CH3:11])[C:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[N:3]1.[CH3:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([CH3:24])[C:20]=1[N:21]([CH3:23])[CH3:22])[CH:16]=[O:17]>O1CCOCC1>[CH3:23][N:21]([CH3:22])[C:20]1[C:19]([CH3:24])=[CH:18][C:15]([CH:16]2[O:17][C:2]([CH3:1])([CH3:11])[N:3]=[C:4]2[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[CH:14][C:13]=1[CH3:12]

Participants

4

Reactant 2

HCID 3082152,2-Dimethyl-3-phenyl-2H-azireneHCID 205177714-(Dimethylamino)-3,5-dimethylbenzaldehyde

Product 1

HCID 30614394-(2,2-Dimethyl-4-phenyl-2,5-dihydro-1,3-oxazol-5-yl)-N,N,2,6-tetramethylaniline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.6 g of 2,2-dimethyl-3-phenyl-2H-azirine and 2,5 g of 3,5-dimethyl-4-(dimethylamino)benzaldehyde were exposed to light for 2 hours in 300 ml of 1,4-dioxane (with the light source described in Example 2). After purification as described in Example 12 and crystallization from n-pentane, there was obtained 5-[4(dimethylamino)-3,5-xylyl]-2,2-dimethyl-4-phenyl-3-oxazoline which melted at 91°-92° C. after drying for 2 hours at 50° C. and 13 Torr.

Workup

  1. customAfter purification
  2. customas described in Example 12 and crystallization from n-pentane

Sources & evidence

ORD record
ord-767941e765a04f2f9b838fad131d10ad
Source dataset
uspto-grants-1982_03
Patent number
US04317914

Reaction notes

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