Hydrochloric Acid → HCID 20060987, compound

HRID 1085132Notes

Reaction equation

HRID 1085132 reaction equation
[Cl:1][C:2]1[N:6]([C:7]2[CH:18]=[CH:17][C:10]([C:11]([CH2:13][C:14]([O-:16])=O)=O)=[CH:9][CH:8]=2)[C:5]([CH3:19])=[N:4][C:3]=1[CH:20]1[O:24]CCO1.[CH3:25][C:26]1[C:31]([CH3:32])=[CH:30][C:29]([NH2:33])=[C:28]([NH2:34])[CH:27]=1.Cl>C1(C)C=CC=CC=1.C1COCC1>[CH3:25][C:26]1[C:31]([CH3:32])=[CH:30][C:29]2[NH:33][C:14](=[O:16])[CH2:13][C:11]([C:10]3[CH:9]=[CH:8][C:7]([N:6]4[C:2]([Cl:1])=[C:3]([CH:20]=[O:24])[N:4]=[C:5]4[CH3:19])=[CH:18][CH:17]=3)=[N:34][C:28]=2[CH:27]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 766354,5-Dimethyl-1,2-phenylenediamineHCID 20060984HCID 20060984, compound

Product 1

HCID 20060987HCID 20060987, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 4-[5-chloro-4-(1,3-dioxolan-2-yl)-2-methylimidazol-1-yl]benzoylacetate from Preparation 5 (155 mg, 0.38 mmol), and 4,5-dimethyl-1,2-diaminobenzene (55 mg, 0.4 mmol) in toluene (4 ml) was heated at reflux for 4.5 hours, then evaporated to dryness and purified by flash chromatography (eluting with ethyl acetate) to afford a pale yellow gum. 1M HCl (2 ml) was added to a solution of the residue in THF (2 ml) and the mixture was heated to 70° C. for 1 hour. The THF was evaporated and the residue was partitioned between aqueous sodium bicarbonate and dichloromethane. The organic layer was dried over magnesium sulphate and evaporated.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4.5 hours
  3. customevaporated to dryness
  4. custompurified by flash chromatography (eluting with ethyl acetate)
  5. customto afford a pale yellow gum
  6. customThe THF was evaporated
  7. customthe residue was partitioned between aqueous sodium bicarbonate and dichloromethane
  8. dry with materialThe organic layer was dried over magnesium sulphate
  9. customevaporated

Sources & evidence

ORD record
ord-dfd893efca834bedb888dacd8689407d
Source dataset
uspto-grants-1991_04
Patent number
US05008263

Reaction notes

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