Phosgene → 3,4-dihydro-6-isocyanato-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine

HRID 2253588Notes

Reaction equation

HRID 2253588 reaction equation
[NH2:1][C:2]1[CH:3]=[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:16](Cl)(Cl)=[O:17]>>[N:1]([C:2]1[CH:3]=[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:16]=[O:17]

Participants

3

Reactant 2

HCID 6371PhosgeneHCID 136490056-amino-4-propargyl-2H-1,4-benzoxazin-3(4H)-one

Product 1

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

Procedure

6-Amino-3,4-dihydro-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-6-isocyanato-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine which is used as the starting material in Example 3. 1H-NMR (CDCl3, 400 MHz): 6.98-6.92 ppm (m, 2H), 6.79 ppm (q, 1H), 4.66 ppm (d, 2H), 4.63 ppm (s, 2H), 2.31 ppm (t, 1H).

Sources & evidence

ORD record
ord-d9100664906b492d95ad144c8fc7ce2e
Source dataset
uspto-grants-1993_08
Patent number
US05232898

Reaction notes

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