Sodium hydride → trans-3,4-dihydro-3-hydroxy-2,2-dimethyl-4-[2-oxofuran-4(5H)-ylamino]-2H-benzopyran-6-carbonitrile

HRID 1460615Notes

Reaction equation

HRID 1460615 reaction equation
[OH:1][C@H:2]1[C@H:7](OC2CCC(=O)C=2)[C:6]2[CH:15]=[C:16]([C:19]#[N:20])[CH:17]=[CH:18][C:5]=2[O:4][C:3]1([CH3:22])[CH3:21].[NH2:23][C:24]1[CH2:28][O:27][C:26](=[O:29])[CH:25]=1.[H-].[Na+]>CS(C)=O>[OH:1][C@H:2]1[C@H:7]([NH:23][C:24]2[CH2:28][O:27][C:26](=[O:29])[CH:25]=2)[C:6]2[CH:15]=[C:16]([C:19]#[N:20])[CH:17]=[CH:18][C:5]=2[O:4][C:3]1([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 129348Sdz pco 400HCID 133748614-amino-5H-furan-2-one

Product 1

HCID 14301306trans-3,4-dihydro-3-hydroxy-2,2-dimethyl-4-[2-oxofuran-4(5H)-ylamino]-2H-benzopyran-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

34,5 mg of the epoxide of example 1 and 17 mg of 4-Amino-2-(5H)-furanone (CAS 92089-08-2) are reacted analogously to example 5 with sodium hydride in dimethylsulfoxide. The usual working up yields yellowish crystalls of the title compound having a m.p. of 182° C. (from ethanol/dichloromethane, decomposition).

Sources & evidence

ORD record
ord-88178ba757f84ac4a21ff08f29b00f81
Source dataset
uspto-grants-1991_12
Patent number
US05071871

Reaction notes

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