Mercuric cyanide → 2,4,6-tricyanophenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranoside

HRID 2372988

Reaction equation

HRID 2372988 reaction equation
[C:1]([C:3]1[C:4]([SH:13])=[C:5]([CH:8]=[C:9]([C:11]#[N:12])[CH:10]=1)[C:6]#[N:7])#[N:2].[C:14]([O:17][C@@H:18]1[C@@H:23]([O:24][C:25](=[O:27])[CH3:26])[C@H:22]([O:28][C:29](=[O:31])[CH3:30])[CH2:21][S:20][C@@H:19]1Br)(=[O:16])[CH3:15].[Hg](C#N)C#N>>[C:14]([O:17][C@@H:18]1[C@@H:23]([O:24][C:25](=[O:27])[CH3:26])[C@H:22]([O:28][C:29](=[O:31])[CH3:30])[CH2:21][S:20][C@H:19]1[S:13][C:4]1[C:3]([C:1]#[N:2])=[CH:10][C:9]([C:11]#[N:12])=[CH:8][C:5]=1[C:6]#[N:7])(=[O:16])[CH3:15]

Participants

4

Reactant 3

HCID 11591Mercuric cyanideHCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromideHCID 147953373,5-Dicyano-2-mercaptobenzonitrile

Product 1

HCID 147953652,4,6-tricyanophenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranosideYield 17%

Procedure

If the procedure described in Preparation I is followed starting from 4.8 g (258.10-3 mol) of 3,5-dicyano-2-mercaptobenzonitrile (Example 17a), 9.71 g (258.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 6.57 g (8.6.10-3 mol) of mercuric cyanide (Hg(CN)2), 2 g (yield: 17%) of the expected product are obtained after crystallization from ether.

Workup

  1. customIf the procedure described in Preparation I

Sources & evidence

ORD record
ord-8ad788e3f0804b7a8ad5a788bec46bc0
Source dataset
uspto-grants-1992_03
Patent number
US05101048

Linked notes

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