Ammonia → HCID 178516937, compound

HRID 1821366Notes

Reaction equation

HRID 1821366 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:19]([NH2:21])=[S:20])=[N:2]1.[C:22](OCCCl)(=[O:24])[CH3:23].N>C(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:19]2[S:20][CH2:23][C:22](=[O:24])[N:21]=2)=[N:2]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 10959beta-Chloroethyl acetateHCID 86628203HCID 86628203, compound

Product 1

HCID 178516937HCID 178516937, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 161 (0.10 g, 0.34 mmol) was added with ethanol (3.0 mL) and chloroethyl acetate (43 μL, 0.41 mmol), and after heating under reflux for 7 hours, the aqueous ammonia was added to stop the reaction. The mixture was extracted with ethyl acetate, concentrated and purified by silica gel column chromatography (hexane/ethyl acetate=4/1 to 1/4), followed by triturating in ethyl acetate to obtain Compound 172 (13 mg, 12%).

Workup

  1. temperatureafter heating
  2. temperatureunder reflux for 7 hours
  3. customthe reaction
  4. extractionThe mixture was extracted with ethyl acetate
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (hexane/ethyl acetate=4/1 to 1/4)
  7. customby triturating in ethyl acetate

Sources & evidence

ORD record
ord-a1d446a98e16403f84da4e2f3cf7f134
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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