1-Fluoro-3-iodo-5-nitrobenzene → 4,4-diethyl-6-(3-fluoro-5-nitrophenylamino)-1-methyl-1H-benzo[d][1,3]oxazin-2(4H)-one

HRID 899202Notes

Reaction equation

HRID 899202 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]([CH3:11])[C:9](=[O:12])[O:8][C:7]([CH2:15][CH3:16])([CH2:13][CH3:14])[C:6]=2[CH:17]=1.[F:18][C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[C:21](I)[CH:20]=1>>[CH2:13]([C:7]1([CH2:15][CH3:16])[C:6]2[CH:17]=[C:2]([NH:1][C:21]3[CH:22]=[C:23]([N+:25]([O-:27])=[O:26])[CH:24]=[C:19]([F:18])[CH:20]=3)[CH:3]=[CH:4][C:5]=2[N:10]([CH3:11])[C:9](=[O:12])[O:8]1)[CH3:14]

Participants

3

Reactant 2

HCID 2590861-Fluoro-3-iodo-5-nitrobenzeneHCID 692163266-amino-4,4-diethyl-1-methyl-1,4-dihydro-2H-3,1-benzoxazin-2-one

Product 1

HCID 111879384,4-diethyl-6-(3-fluoro-5-nitrophenylamino)-1-methyl-1H-benzo[d][1,3]oxazin-2(4H)-one

Procedure

Prepared from 6-amino-4,4-diethyl-1-methyl-1,4-dihydro-2H-3,1-benzoxazin-2-one and 1-fluoro-3-iodo-5-nitrobenzene according to the coupling protocol of example 2. 1H NMR (DMSO-d6): δ 8.92 (s, 1H), 7.53 (t, J=1.8 Hz, 1H), 7.36 (dt, J=8.6, 2.2 Hz, 1H), 7.21 (dd, J=8.7, 2.4 Hz, 1H), 7.12 (d, J=8.7 Hz, 1H), 7.06 (d, J=2.4 Hz, 1H), 7.03 (dt, J=11.1, 2.2 Hz, 1H), 3.29 (s, 3H), 2.01 (m, 4H), 0.82 (t, J=7.3 Hz, 6H); MS (ESI) m/z 374 ([M+H]+); MS (ESI) m/z 372 ([M−H]−); Anal. calcd for C19H20FN3O4: C, 61.12; H, 5.40; N, 11.25. Found: C, 60.33; H, 5.17; N, 10.51.

Sources & evidence

ORD record
ord-9ef39dc8c0c7416080069bd61c9db5a0
Source dataset
uspto-grants-2008_04
Patent number
US07354915B2

Reaction notes

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