1-(1-Isocyanato-1-methylethyl)-3-(1-methylethenyl)benzene → Coumarin

HRID 1421347Notes

Reaction equation

HRID 1421347 reaction equation
N(C(C1C=C(C=CC=1)C(C)=C)(C)C)=C=O.OCCCCCCOC([C:26]1[C:27](=[O:41])[O:28][C:29]2[C:34]([CH:35]=1)=[CH:33][CH:32]=[C:31](N(CC)CC)[CH:30]=2)=O.C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC>C(Cl)Cl>[O:28]1[C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:35]=[CH:26][C:27]1=[O:41]

Participants

5

Reactant 3

HCID 6041521-(1-Isocyanato-1-methylethyl)-3-(1-methylethenyl)benzeneHCID 9809426Di-n-butyldilauryltinHCID 15346017HCID 15346017, compound

Product 1

HCID 323Coumarin

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In this scheme, m-(2-isocyanatoprop-2-yl)-α-methylstyrene (23) and m/p-methylstyrene (24) are polymerised under the action of AIBN as free-radical initiator in toluene at 100 to 110° C. to yield the copolymer (25). The preferred molar proportion x of comonomer (23) is between 0 and 60%. The copolymer (25) obtainable in this manner reacts with 3-(6-hydroxyhexoxycarbonyl)-7-diethylaminocoumarin (26) in the presence of catalytic quantities of dibutyltin dilaurate (DBZD) in refluxing methylene chloride, wherein the copolymer (27) may be obtained with a lateral coumarin luminophore (Et=ethyl).

Sources & evidence

ORD record
ord-268c01bca7d745c5a123aa326b9a78d1
Source dataset
uspto-grants-2000_06
Patent number
US06075106

Reaction notes

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