Phenyl isocyanate → (5RS, 6SR)-6-phenyl-5-phenylcarbamoyloxy-2-(2-thienyl)-5,6-dihydro-4H-1,3-oxazine

HRID 982257Notes

Reaction equation

[C:1]1([CH:7]2[O:12][C:11]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[N:10][CH2:9][CH:8]2[OH:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:19]1([N:25]=[C:26]=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[C:1]1([CH:7]2[O:12][C:11]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[N:10][CH2:9][CH:8]2[O:18][C:26](=[O:27])[NH:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 2

HCID 7672Phenyl isocyanate

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

Product 1

HCID 14650703(5RS, 6SR)-6-phenyl-5-phenylcarbamoyloxy-2-(2-thienyl)-5,6-dihydro-4H-1,3-oxazineYield 77.4%

Procedure

Working in a manner similar to that described in Example 12, but starting with (5RS, 6SR)-6-phenyl-2-(2-thienyl)-5,6-dihydro-4H-1,3-oxazin-5-ol (1.55 g) and phenyl isocyanate (0.8 g), and after recrystallization in isopropanol, (5RS, 6SR)-6-phenyl-5-phenylcarbamoyloxy-2-(2-thienyl)-5,6-dihydro-4H-1,3-oxazine (1.75 g), m.p. 98° C., is obtained.

Workup

customafter recrystallization in isopropanol

Sources & evidence

ORD record: ord-2ed86a68dbc64c41b093204cb75cf510
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04994569

Reaction notes

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