Sodium hydride → trans-3,4-dihydro-3-hydroxy-2,2-dimethyl-4-[N-methyl-N-(N-methyl-2-oxo-pyrrol-4(5H)-yl)amino]-2 H-1-benzopyran-6-carbonitrile

HRID 1460618Notes

Reaction equation

HRID 1460618 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].[H-].[Na+].[CH3:25][NH:26][C:27]1[CH2:31][N:30]([CH3:32])[C:29](=[O:33])[CH:28]=1>CS(C)=O>[OH:1][C@H:2]1[C@H:7]([N:26]([CH3:25])[C:27]2[CH2:31][N:30]([CH3:32])[C:29](=[O:33])[CH:28]=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 143013504-(N-methyl-amino)-N-methyl-2(5H)-pyrrolon

Product 1

HCID 14301314trans-3,4-dihydro-3-hydroxy-2,2-dimethyl-4-[N-methyl-N-(N-methyl-2-oxo-pyrrol-4(5H)-yl)amino]-2 H-1-benzopyran-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

402 mg of the epoxide of example 1 in 4 ml of dimethylsulfoxide are reacted analogously to example 5 with 60 mg of sodium hydride and 25.2 mg of the amide obtained above. Usual work up yields the title compound having a m.p. of 266°-69° C.

Workup

  1. customobtained above

Sources & evidence

ORD record
ord-531a850a58ac49578d369115c2acfe28
Source dataset
uspto-grants-1991_12
Patent number
US05071871

Reaction notes

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