Aniline → 6-Benzyl-5,6-dihydro-4-hydroxy-2-methyl-1,1-dioxo-N-phenyl-2H-1,2,6-thiadiazine-3-carboxamide

HRID 35846Notes

Reaction equation

HRID 35846 reaction equation
[CH2:1]([N:8]1[S:13](=[O:15])(=[O:14])[N:12]([CH3:16])[C:11]([C:17]([O:19]C)=O)=[C:10]([OH:21])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:1]([N:8]1[S:13](=[O:14])(=[O:15])[N:12]([CH3:16])[C:11]([C:17]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:19])=[C:10]([OH:21])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 54719673methyl 6-benzyl-5,6-dihydro-4-hydroxy-2-methyl-1,1-dioxo-2H-1,2,6-thiadiazine-3-carboxylate

Product 1

HCID 547196726-Benzyl-5,6-dihydro-4-hydroxy-2-methyl-1,1-dioxo-N-phenyl-2H-1,2,6-thiadiazine-3-carboxamideYield 54%

Procedure

The synthesis is effected analogously to Example 1 using in each case 1 equivalent of methyl 6-benzyl-5,6-dihydro-4-hydroxy-2-methyl-1,1-dioxo-2H-1,2,6-thia-diazine-3-carboxylate and aniline. Recrystallisation from a diisopropyl ether/acetone mixture gives the title compound in a yield of 54%.

Workup

  1. customRecrystallisation from a diisopropyl ether/acetone mixture

Sources & evidence

ORD record
ord-85b34e73c2644d82b2c88c6b7e5732d4
Source dataset
uspto-grants-1995_05
Patent number
US05411955

Reaction notes

Loading…