Bis-(1H-imidazol-2-YL)-methanone → 6-Bromospiro[4H-3,1-benzoxazine-4,1'-cyclohexan]-2(1H)-one

HRID 1882800Notes

Reaction equation

HRID 1882800 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9]1([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[C:16](C1NC=CN=1)(C1NC=CN=1)=[O:17]>>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:16](=[O:17])[O:15][C:9]3([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]3)[C:3]=2[CH:4]=1

Participants

3

Reactant 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 235096031-(2-Amino-5-bromo-phenyl)cyclohexanol

Product 1

HCID 220219046-Bromospiro[4H-3,1-benzoxazine-4,1'-cyclohexan]-2(1H)-one

Procedure

Prepared from 1-(2-amino-5-bromo-phenyl)cyclohexanol and carbonyl diimidazole according to the procedure of Example 2. Off-white solid: mp 208-210° C. 1H-NMR (DMSO-d6) δ10.26 (s, 1H), 7.45 (d, 1H, J=2.2 Hz), 7.39 (dd, 1H, J=8.2, 2.2 Hz), 6.81 (d, 1H, J=8.3 Hz), 1.90-1.97 (m, 2H), 1.80-1.85 (m, 5H), 1.25-1.35 (m, 1H); MS (APCI) m/z 296 ([M+H]+, 68%)

Sources & evidence

ORD record
ord-6d68d225ddfb4f8aa89af065a4c6c8f2
Source dataset
uspto-grants-2004_07
Patent number
US06759408B2

Reaction notes

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