4-Bromobenzyl isocyanate → HCID 10029702, compound

HRID 887213Notes

Reaction equation

HRID 887213 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]=[C:10]=[O:11])=[CH:4][CH:3]=1.[NH2:12][C:13]1[C:22]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[CH:16][N:17]=[CH:18]2>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH:9][C:10]([NH:12][C:13]2[C:22]([C:23]([OH:32])([C:28]([F:31])([F:29])[F:30])[C:24]([F:25])([F:26])[F:27])=[CH:21][CH:20]=[C:19]3[C:14]=2[CH:15]=[CH:16][N:17]=[CH:18]3)=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 43746174-Bromobenzyl isocyanateHCID 22032598HCID 22032598, compound

Product 1

HCID 10029702HCID 10029702, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared using 1-bromo-4-(isocyanatomethyl)benzene, the product of Example 77A and the procedure described in Example 73B except that THF was used as solvent (white solid, 840 mg, 34%). MS (ESI+) m/z 376 (M+H)+; MS (ESI−) m/z 374 (M−H)−; 1H NMR (DMSO-d6, 300 MHz) δ 4.35 (d, 5.8, 2H), 7.12 (m, 1H), 7.18 (m, 2H), 7.40 (m, 1H), 7.91 (d, J 8.5, 1H), 7.99 (d, J 6.1, 1H), 8.24 (d, J 8.5, 1H), 8.69 (d, J 5.8, 1H), 8.88 (s, 1H), 9.44 (s, 1H); Anal. Calcd for C20H14BrF6N3O2: C, 46.00; H, 3.50; N, 11.23. Found: C, 54.61; H, 3.35; N, 11.14.

Sources & evidence

ORD record
ord-20caa0927b874a75913c8d0448728965
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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