Ammonium Chloride → HCID 59411378, compound

HRID 453584Notes

Reaction equation

HRID 453584 reaction equation
[O-][CH2:2]C.[Na+].C([C:7]1[S:11][C:10]([CH3:12])=[C:9]([CH2:13][NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:8]=1)=O.[N:25]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[N+]=[N-].[Cl-].[NH4+]>C(O)C>[CH2:17]([O:16][C:15]([N:14]([CH3:2])[C:13]1[C:9]2[NH:25][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:12][C:10]=2[S:11][C:7]=1[CH3:8])=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 69480Acetic acid, azido-, ethyl esterHCID 2723922Sodium ethoxideHCID 86643546HCID 86643546, compound

Product 1

HCID 59411378HCID 59411378, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution (20 mL) of sodium ethoxide (0.68 g) in ethanol was added dropwise a mixture of benzyl (5-formyl-2-methyl-3-thienyl)methylcarbamate (0.72 g) and ethyl azidoacetate (1.3 g) under ice-cooling. After the completion of the dropwise addition, the mixture was stirred for 1 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was concentrated. The obtained residue was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was dissolved in toluene (20 mL), and the mixture was stirred at 110° C. for 2 hr. The reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography to give ethyl 3-{[(benzyloxy)carbonyl](methyl)amino}-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate (91 mg, yield 10%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio). melting point 122° C.

Workup

  1. temperaturecooling
  2. additionAfter the completion of the dropwise addition
  3. concentrationthe mixture was concentrated
  4. extractionThe obtained residue was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. dissolutionThe obtained residue was dissolved in toluene (20 mL)
  9. stirringthe mixture was stirred at 110° C. for 2 hr
  10. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-a1f0306e8cf64fd68d4bb6bab94f6f6f
Source dataset
uspto-grants-2013_07
Patent number
US08492405B2

Reaction notes

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