Ethyl 3-amino-4,4,4-trifluorocrotonate → 6-{3-[2-(ethoxycarbonyl)-1-trifluoromethyl-vinyl]ureido}-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine

HRID 2253578Notes

Reaction equation

HRID 2253578 reaction equation
[NH2:1]/[C:2](/[C:9]([F:12])([F:11])[F:10])=[CH:3]\[C:4]([O:6][CH2:7][CH3:8])=[O:5].[N:13]([C:16]1[CH:17]=[CH:18][C:19]2[O:24][CH2:23][C:22](=[O:25])[N:21]([CH2:26][C:27]#[CH:28])[C:20]=2[CH:29]=1)=[C:14]=[O:15]>>[CH2:7]([O:6][C:4]([CH:3]=[C:2]([NH:1][C:14](=[O:15])[NH:13][C:16]1[CH:17]=[CH:18][C:19]2[O:24][CH2:23][C:22](=[O:25])[N:21]([CH2:26][C:27]#[CH:28])[C:20]=2[CH:29]=1)[C:9]([F:10])([F:11])[F:12])=[O:5])[CH3:8]

Participants

3

Reactant 2

HCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonateHCID 197458273,4-dihydro-6-isocyanato-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine

Product 1

HCID 543072216-{3-[2-(ethoxycarbonyl)-1-trifluoromethyl-vinyl]ureido}-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine

Procedure

Analogously to the procedure described in Example 1, starting from ethyl 3-amino-4,4,4-trifluorocrotonate and 3,4-dihydro-6-isocyanato-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine there is obtained 6-{3-[2-(ethoxycarbonyl)-1-trifluoromethyl-vinyl]ureido}-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine (not isolated) and, after cyclization of this benzoxazine, there is obtained 3-[3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl]-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione, m.p. >250° C.

Sources & evidence

ORD record
ord-c5b0c6b155ae46e7a07fa0003f8dae9b
Source dataset
uspto-grants-1993_08
Patent number
US05232898

Reaction notes

Loading…