Mercuric cyanide → N-[2-Methyl-5-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxymethyl)-phenyl]-3-nitrobenzamide

HRID 965130

Reaction equation

HRID 965130 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:21])=[C:7]([NH:9][C:10](=[O:20])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[CH:8]=1.[Hg](C#N)C#N.[C:27]([OH:30])(=[O:29])[CH3:28].[C:31]([OH:34])(=[O:33])[CH3:32].[C:35]([OH:38])(=[O:37])[CH3:36].[C:39]([OH:42])(=[O:41])[CH3:40].[C@H:43]1(Br)[O:51][C@H:50]([CH2:52]O)[C@@H:48](O)[C@H:46](O)[C@H:44]1O.[K+].[Br-]>[N+](C)([O-])=O.[Hg](Br)Br>[CH3:21][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][O:1][C@@H:43]2[O:51][C@H:50]([CH2:52][O:41][C:39](=[O:42])[CH3:40])[C@@H:48]([O:37][C:35](=[O:38])[CH3:36])[C@H:46]([O:33][C:31](=[O:34])[CH3:32])[C@H:44]2[O:29][C:27](=[O:30])[CH3:28])=[CH:8][C:7]=1[NH:9][C:10](=[O:20])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1

Participants

7

Reactant 4

HCID 11591Mercuric cyanideHCID 253877Potassium BromideHCID 19074226N-(5-Hydroxymethyl-2-methylphenyl)-3-nitrobenzamideHCID 86752853alpha-D-glucopyranosyl bromide tetraacetate

Product 1

HCID 67578982N-[2-Methyl-5-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxymethyl)-phenyl]-3-nitrobenzamideYield 57.2%

Reagents, catalysts & solvents 2

HCID 24612Mercury dibromideCatalystHCID 6375NitromethaneSolvent

Procedure

A mixture of N-(5-hydroxymethyl-2-methylphenyl)-3-nitrobenzamide (10.0 g, 0.034 mol), HgBr2 (10.0 g, 0.041 mol), Hg(CN)2 (15.0 g, 0.058 mol), and α-D-glucopyranosyl bromide tetraacetate (17.2 g, 0.042 mol) in nitromethane (200 mL) was heated under reflux for 4 h. 2.0M KBr was added and the mixture was stirred for 30 minutes and extracted with EtOAc. The combined extracts were washed with saturated aqueous NaHCO3 and brine, dried (MgSO4), and concentrated to give 12.0 g (56%) of product as a brown foam; 1H NMR (DMSO-d6) δ2.00 (m, 12 H), 2.21 (s, 3 H), 4.00 (m, 2 H), 4.20 (dd, J=12.4, 5.0 Hz, 1 H), 4.58 (d, J=12.4 Hz, 1 H), 4.82 (m, 4 H), 5.27 (t, J=9.3 Hz, 1 H), 7.10 (d, J=7.8 Hz, 1 H), 7.24 (d, J=7.8 Hz, 1 H), 7.25 (s, 1 H), 7.81 (m, 1 H), 8.42 (m, 2 H), 8.80 (s, 1 H), 10.60 (s, 1 H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 h
  3. extractionextracted with EtOAc
  4. washThe combined extracts were washed with saturated aqueous NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-233692c36e1f45f28397fc029598e4b7
Source dataset
uspto-grants-1998_06
Patent number
US05773420

Linked notes

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