Chloroform → HCID 9150812, compound

HRID 2352305Notes

Reaction equation

HRID 2352305 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:5][CH:4]=1.[H][H].C(Cl)(Cl)Cl>C(O)C.[Pd]=O>[NH2:21][C:18]1[CH:17]=[CH:16][C:15]([S:12]([NH:11][CH2:10][CH2:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)(=[O:13])=[O:14])=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 6212ChloroformHCID 737618HCID 737618, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9150812HCID 9150812, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 5083724Palladium monoxideCatalystHCID 702EthanolSolvent

Procedure

A solution of the product of stage (i) (4.5 g) in ethanol (150 ml) was hydrogenated at room temperature and pressure over 10% palladium oxide on charcoal (50% aq. paste, 0.5 g) for 2 h until hydrogen uptake ceased (1000 ml). Chloroform (150 ml) was added, and the mixture stirred until the product dissolved. The catalyst was filtered off, washed with ethanol, and the filtrate evaporated in vacuo to give a solid (3.8 g). A sample (0.2 g) was purified by flash chormatography eluted with chloroform:methanol (50:1) to give the title compound as a solid (0.11 g). m.p. 144°-146°.

Workup

  1. customwas hydrogenated at room temperature
  2. dissolutiondissolved
  3. filtrationThe catalyst was filtered off
  4. washwashed with ethanol
  5. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-fcadc26e32da450b85c6d461a2ad7069
Source dataset
uspto-grants-1989_10
Patent number
US04876267

Reaction notes

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