3-Bromophenyl isocyanate → 7-Benzyloxy-4-hydroxy-8-methyl-3-(3'-bromophenylcarbamoyl]coumarin

HRID 55334

Reaction equation

HRID 55334 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([CH3:19])=[C:17]2[C:12]([C:13]([OH:21])=[CH:14][C:15](=[O:20])[O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:22][C:23]1[CH:24]=[C:25]([N:29]=[C:30]=[O:31])[CH:26]=[CH:27][CH:28]=1>C(N(CC)CC)C>[CH2:1]([O:8][C:9]1[C:18]([CH3:19])=[C:17]2[C:12]([C:13]([OH:21])=[C:14]([C:30](=[O:31])[NH:29][C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([Br:22])[CH:24]=3)[C:15](=[O:20])[O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1410013-Bromophenyl isocyanateHCID 546941307-(Benzyloxy)-4-hydroxy-8-methyl-2H-1-benzopyran-2-one

Product 1

HCID 867507747-Benzyloxy-4-hydroxy-8-methyl-3-(3'-bromophenylcarbamoyl]coumarinYield 15.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

According to the procedure of example 2, 7-benzyloxy-4-hydroxy-8-methylcoumarin (0.813 g, 2.88 mmol) and 3-bromophenylisocyanate (0.39 ml, 3.12 mmol) were reacted in the presence of triethylamine (0.1 ml) to generate the title compound as an off-white solid, mp 229°-231° C., (0.211 g, 0.44 mmol, yield 15.2%). Analysis: Calculated for C24H18NO5Br: C, 601.13; H, 3.76; N, 2.92. Found: C, 60.04; H, 3.51; N, 2.89. 1H NMR (CDCl3): 7.94 (br s, 1H), 7.87 (d, J=9.0 Hz, 1H), 7.48 (d, J=7.6 Hz, 1H), 7.41 (m, 5H), 7.24 (m, 2H), 6.97 (d, J=9.0 Hz, 1H), 5.21 (s, 2H), 2.36 (s, 3H).

Sources & evidence

ORD record
ord-9d0f2ca452904712bd3e36e82492984c
Source dataset
uspto-grants-1997_04
Patent number
US05624951

Linked notes

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