Ammonia → HCID 178486828, compound

HRID 720346Notes

Reaction equation

HRID 720346 reaction equation
C(OCC([NH:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[C:14]=1[NH:25][C:26](=O)[CH2:27][O:28]CC1C=CC=CC=1)=O)C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CO.N>C1(C)C(C)=CC=CC=1>[OH:28][CH2:27][C:26]1[NH:25][C:14]2[C:15]([O:23][CH3:24])=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:13]=2[N:12]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 86587495HCID 86587495, compound

Product 1

HCID 178486828HCID 178486828, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

1,2-Di(benzyloxyacetamido)-3,4,5-trimethoxybenzene (1.9 g) was dissolved in xylene (30 mL), p-toluenesulfonic acid monohydrate (2.0 g) was added to the solution, and the mixture was stirred for 3 hours under reflux. After cooling, methanol saturated with ammonia was added to the reaction mixture into a uniform solution. The solution was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (chloroform:methanol=15:1 to 10:1) to obtain the title compound.

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. concentrationThe solution was concentrated under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel (chloroform:methanol=15:1 to 10:1)

Sources & evidence

ORD record
ord-15ee82f37ac746bc94c513c10e3dc954
Source dataset
uspto-grants-2006_11
Patent number
US07135473B2

Reaction notes

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