1-Chloro-4-(isocyanatomethyl)benzene → HCID 57658767, compound

HRID 910050Notes

Reaction equation

HRID 910050 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[CH2:14][NH:15][CH2:16][C:17]([O:19]CC)=O)C.[Cl:23][C:24]1[CH:33]=[CH:32][C:27]([CH2:28][N:29]=[C:30]=[O:31])=[CH:26][CH:25]=1>>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:3])=[O:22])=[C:8]([CH2:14][N:15]2[CH2:16][C:17](=[O:19])[N:29]([CH2:28][C:27]3[CH:32]=[CH:33][C:24]([Cl:23])=[CH:25][CH:26]=3)[C:30]2=[O:31])[CH:9]=1

Participants

3

Reactant 2

HCID 33723791-Chloro-4-(isocyanatomethyl)benzeneHCID 57658774HCID 57658774, compound

Product 1

HCID 57658767HCID 57658767, compound

Procedure

Prepared from 4-bromo-2-[(ethoxycarbonylmethylamino)methyl]phenoxyacetic acid ethyl ester (235 mg, 0.63 mmol) and 4-chlorobenzylisocyanate (166 μL, 1.26 mmol) according to GP12 (yield: 183.4 mg, 62%): LC/MS (an10p8): Rt 2.3 min, m/z 465 [M−H]−; 1H NMR (DMSO-d6): δ 4.05 (s, 2H), 4.48 (s, 2H), 4.55 (s, 2H), 4.73 (s, 2H), 6.92 (d, J=8.3 Hz, 1H), 7.25-7.45 (m, 6H), 13.11 (br. s, 1H).

Sources & evidence

ORD record
ord-2294fd7ea68c4ab5b9ccf17a6b9a173e
Source dataset
uspto-grants-2011_09
Patent number
US08022063B2

Reaction notes

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