Hexamethylenetetramine → HCID 178497565, compound

HRID 579459Notes

Reaction equation

HRID 579459 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:14][C:13]3[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:12]=3[N:11]=2)=[CH:6][CH:5]=1.C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:34](O)=[O:35]>>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:5]=[CH:6][C:7]([C:10]2[NH:14][C:13]3[C:15]([CH:34]=[O:35])=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:12]=3[N:11]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 4915285HCID 4915285, compound

Product 1

HCID 178497565HCID 178497565, compoundYield 21%

Conditions

Temperature
130 °C

Procedure

A mixture of 4-(6-Methoxy-1H-benzoimidazol-2-yl)-benzoic acid methyl ester (1.50 g, 5.3 mmol), hexamethylenetetramine (1.50 mg, 10.60 mmol) and trifluoroacetic acid (12 mL) was stirred in a closed vessel under an argon atmosphere at 130° C. for 3 h. The resultant brown solution was poured onto 250 mL of crushed ice. The mixture was extracted with, chloroform-ethanol 95:5 (2×0.100 mL). The combined organic layers were dried (Na2SO4), and evaporated. The solid residue was purified by column chromatography over silica (Kieselgel 60) using chloroform as the eluent to give title compound (350 mg, 1.13 mmol, 21%) yellow crystals.

Workup

  1. extractionThe mixture was extracted with, chloroform-ethanol 95:5 (2×0.100 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. customevaporated
  4. customThe solid residue was purified by column chromatography over silica (Kieselgel 60)

Sources & evidence

ORD record
ord-51aa9600005848e68cf2077aa9169cb5
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

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