Phosgene → 7-fluoro-6-isocyanato-4-propargyl-2H-1,4-benzoxazin-3(4H)-one

HRID 2253587Notes

Reaction equation

HRID 2253587 reaction equation
[NH2:1][C:2]1[C:3]([F:16])=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[N:7]([CH2:12][C:13]#[CH:14])[C:6]=2[CH:15]=1.[C:17](Cl)(Cl)=[O:18]>>[F:16][C:3]1[C:2]([N:1]=[C:17]=[O:18])=[CH:15][C:6]2[N:7]([CH2:12][C:13]#[CH:14])[C:8](=[O:11])[CH2:9][O:10][C:5]=2[CH:4]=1

Participants

3

Reactant 2

HCID 6371PhosgeneHCID 111603236-amino-7-fluoro-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-3-one

Product 1

HCID 118174397-fluoro-6-isocyanato-4-propargyl-2H-1,4-benzoxazin-3(4H)-one

Procedure

6-Amino-3,4-dihydro-7-fluoro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine is treated with phosgene analogously to the procedure described in Example 103 in order to produce the 3,4-dihydro-7-fluoro-6-isocyanato-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine which is used as the starting material in Example 2. 1H-NMR (CDCl3, 60 MHz): 7.02 ppm (d, 1H), 6.88 ppm (d, 1H), 4.88-4.60 ppm (m, 4H), 2.35 ppm (t, 1H).

Sources & evidence

ORD record
ord-72c259f01e514eddaa3460c2ce5b8da3
Source dataset
uspto-grants-1993_08
Patent number
US05232898

Reaction notes

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