Sulfuric Acid → HCID 178479471, compound

HRID 1702608

Reaction equation

HRID 1702608 reaction equation
[ClH:1].[NH:2]([CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]([OH:15])=[O:14])[CH2:9][CH2:8]1)[C:3]([NH2:5])=[NH:4].[CH:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1O.S(=O)(=O)(O)O.B(O)(O)O>CS(C)=O.C1(C)C(C)=CC=CC=1>[ClH:1].[NH:2]([CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]([O:15][C:18]2[CH:17]=[CH:16][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)=[O:14])[CH2:9][CH2:8]1)[C:3]([NH2:5])=[NH:4]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 7628Boric AcidHCID 86632-NaphtholHCID 178479474HCID 178479474, compound

Product 1

HCID 178479471HCID 178479471, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 7237O-XyleneSolvent

Procedure

A suspension of trans-4-guanidinomethylcyclohexanecarboxylic acid hydrochloride(1.8 g), β-naphtol(1.44 g), sulfuric acid(0.05 g) and boric acid(0.03 g) in a mixture of dimethylsulfoxide(10 ml) and xylene(50 ml) was heated under reflux conditions for 20 hours. The resulting water was removed by azeotropy with xylene. Following concentration of the reaction mixture, the residue was chromatographed on a column of silica gel with chloroform/methanol as eluent to give the title compound.

Workup

  1. temperaturewas heated under reflux conditions for 20 hours
  2. customThe resulting water was removed by azeotropy with xylene
  3. customthe residue was chromatographed on a column of silica gel with chloroform/methanol as eluent

Sources & evidence

ORD record
ord-86b2ed1f7018499bbbc39add10230690
Source dataset
uspto-grants-1982_09
Patent number
US04348410

Linked notes

Loading…