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

HRID 2198941Notes

Reaction equation

HRID 2198941 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:20]=[C:19]([N:21]([CH3:23])[CH3:22])[CH:18]=[C:17]([CH3:24])[C:14]=1[CH:15]=[O:16]>O1CCOCC1>[CH3:23][N:21]([CH3:22])[C:19]1[CH:20]=[C:13]([CH3:12])[C:14]([CH:15]2[O:16][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)=[C:17]([CH3:24])[CH:18]=1

Participants

4

Reactant 2

HCID 3082152,2-Dimethyl-3-phenyl-2H-azireneHCID 197876914-(Dimethylamino)-2,6-dimethylbenzaldehyde

Product 1

HCID 30614404-(2,2-Dimethyl-4-phenyl-2,5-dihydro-1,3-oxazol-5-yl)-N,N,3,5-tetramethylaniline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.25 g of 2,2-dimethyl-3-phenyl-2H-azirine and 2 g of 2,6-dimethyl-4-(dimethylamino)benzaldehyde were exposed to light for 3 hours in 350 ml of 1,4-dioxane (with the light source described in Example 2). After purification as described in Example 11 and crystallization from n-pentane, there was obtained 5-[4-(dimethylamino)-2,6-xylyl]-2,2-dimethyl-4-phenyl-3-oxazoline which melted at 105° C. after drying for 4 hours at 60° C. and 13 Torr.

Workup

  1. customAfter purification
  2. customas described in Example 11 and crystallization from n-pentane

Sources & evidence

ORD record
ord-fb6e7b2a5fc7474fbf483b214e6ed604
Source dataset
uspto-grants-1982_11
Patent number
US04360530

Reaction notes

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