Sodium Iodide → 1-Benzyloxy-3-[3-chloro-4-(3-nitropropyl)phenylthio]benzene

HRID 1714587Notes

Reaction equation

HRID 1714587 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]=[CH:23][C:24](OCC)=O)=[C:18]([Cl:29])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Bi](Cl)(Cl)Cl.[BH4-].[Na+].[BH4-].[K+].[Cl-].[Li+].CS(Cl)(=O)=O.[I-].[Na+].[N:47]([O-:49])=[O:48].[Na+]>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][N+:47]([O-:49])=[O:48])=[C:18]([Cl:29])[CH:17]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 8

HCID 5238Sodium IodideHCID 24591Bismuth trichlorideHCID 31297Methanesulfonyl chlorideHCID 433294Lithium ChlorideHCID 4192641Potassium borohydrideHCID 4311764Sodium borohydrideHCID 23668193Sodium NitriteHCID 59464778Ethyl 3-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]acrylate

Product 1

HCID 115098671-Benzyloxy-3-[3-chloro-4-(3-nitropropyl)phenylthio]benzene

Procedure

The process of the present invention, which enables industrial scale production of Compound I, is carried out as follows (See also Scheme I): Ethyl 3-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]acrylate is reduced using bismuth trichloride and sodium borohydride. The reduced product is further reduced using potassium borohydride and lithium chloride. The resulting alcohol derivative is mesylated by reacting with methanesulfonyl chloride. The mesylated product is iodinated with sodium iodide and then reacted with sodium nitrite to form 1-benzyloxy-3-[3-chloro-4-(3-nitropropyl)phenylthio]benzene. This product is reacted with formaldehyde in the presence of a base to form 2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]ethyl]-2-nitro-1,3-propanediol. Reducing this compound with palladium hydroxide-carbon gives Compound I.

Sources & evidence

ORD record
ord-450ba1384c874d23ad9dd3fcb00294e0
Source dataset
uspto-grants-2010_09
Patent number
US07795472B2

Reaction notes

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