(E)-N-cinnamyl-2-thiophenecarboxamide → (5RS, 6SR)-6-phenyl-2-(2-thienyl)-5,6-dihydro-4H-1,3-oxazin-5-ol

HRID 982258Notes

Reaction equation

HRID 982258 reaction equation
F[C:2]1[CH:7]=[CH:6]C=C[C:3]=1[C:8]1[O:9][CH:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:11]([OH:14])[CH2:12][N:13]=1.C(NC(C1[S:34]C=CC=1)=O)/C=C/C1C=CC=CC=1>>[C:15]1([CH:10]2[O:9][C:8]([C:3]3[S:34][CH:6]=[CH:7][CH:2]=3)=[N:13][CH2:12][CH:11]2[OH:14])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 14650587(E)-N-cinnamyl-2-thiophenecarboxamideHCID 14650610(5RS, 6SR)-2-(2-fluorophenyl)-6-phenyl-5,6-dihydro-4H-1,3-oxazin-5-ol

Product 1

HCID 14650616(5RS, 6SR)-6-phenyl-2-(2-thienyl)-5,6-dihydro-4H-1,3-oxazin-5-ol

Procedure

(5RS, 6SR)-6-Phenyl-2-(2-thienyl)-5,6-dihydro-4H-1,3-oxazin-5-ol may be obtained in the following manner: working as described in Example 22 for the preparation of (5RS, 6SR)-2-(2-fluorophenyl)-6-phenyl-5,6-dihydro-4H-1,3-oxazin-5-ol, but starting with (E)-N-cinnamyl-2-thiophenecarboxamide (5 g), a 0.55 M solution (38 cc) of 3-chloroperbenzoic acid in dichloromethane and boron trifluoride etherate (3.2 g), and after recrystallization in dichloromethane, (5RS, 6SR)-6-phenyl-2-(2-thienyl)-5,6-dihydro-4H-1,3-oxazin-5-ol (2.9 g), m.p. 158° C., is obtained.

Workup

  1. customa 0.55 M solution (38 cc) of 3-chloroperbenzoic acid in dichloromethane and boron trifluoride etherate (3.2 g), and after recrystallization in dichloromethane

Sources & evidence

ORD record
ord-fd7260c93bca4756801bfc253c99a2c9
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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