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

HRID 6005

Reaction equation

[SH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Hg](C#N)C#N.[C:15]([O:18][C@@H:19]1[C@@H:24]([O:25][C:26](=[O:28])[CH3:27])[C@H:23]([O:29][C:30](=[O:32])[CH3:31])[CH2:22][S:21][C@@H:20]1Br)(=[O:17])[CH3:16]>>[C:15]([O:18][C@@H:19]1[C@@H:24]([O:25][C:26](=[O:28])[CH3:27])[C@H:23]([O:29][C:30](=[O:32])[CH3:31])[CH2:22][S:21][C@H:20]1[S:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5])(=[O:17])[CH3:16]

Participants

Reactant 3

HCID 11591Mercuric cyanide

HCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide

HCID 110189262-Mercaptobenzonitrile

Product 1

HCID 147953452-cyanophenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranosideYield 50%

Procedure

If the procedure described in Preparation I is followed starting from 9.70 g (72.10-3 mol) of 2-mercaptobenzonitrile, 19.45 g (77.10-3 mol) of mercuric cyanide, Hg(CN)2, and 27.4 g (77.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 14.7 g (yield: 50%) of the expected product are obtained.

Workup

customIf the procedure described in Preparation I

Sources & evidence

ORD record: ord-9b0f85be4c6140d5896fab7059cbf008
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05246961

Linked notes

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