Hydrochloric Acid → HCID 10693387, compound

HRID 1421392Notes

Reaction equation

HRID 1421392 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[C:10]=2[N:20]([C:24]2[CH:29]=[CH:28][C:27]([O:30]CC3C=CC=CC=3)=[CH:26][CH:25]=2)[C:21](=[O:23])[CH3:22])=[CH:5][CH:4]=1.Cl>CCO.CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[C:10]=2[N:20]([C:24]2[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=2)[C:21](=[O:23])[CH3:22])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10505851HCID 10505851, compound

Product 1

HCID 10693387HCID 10693387, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

2-(4-Methoxyphenyl)-3-[N-(4-benzyloxyphenyl)acetamido]-6-methoxy-benzo[b]thiophene (2.43 g, 4.77 mmol) was dissolved in 50 mL of 1:1 EtOH/EtOAc containing 5% con. HCl. To this solution was added 1.0 g of 5% Pd/C. The resulting mixture was hydrogenated at 40 psi for 4 h. The mixture was then filtered through Celite to remove the catalyst. The filtrate was concentrated in vacuo to a semi-solid. Chromatograhy (SiO2, CHl3) provided 1.32 g (83%) of 2-(4-methoxyphenyl)-3-[N-(4-hydroxyphenyl)acetamido]-6-methoxy-benzo[b]thiophene as an amber foam. 1H NMR (DMSO-d6) δ (doubling due to amide rotamers) 9.53 and 9.36 (s, 1H), 7.62-6.51 (m, 11 H), 3.78 and 3.58 (s, 6H), 2.01 and 1.76 (s, 3H). FD mass spec: 419. Anal. Calcd. for C24H21NO4S.0.19 CHCl3 : C, 65.71; H, 4.83; N, 3.17. Found: C, 65.80; H, 4.70; N, 3.01.

Workup

  1. filtrationThe mixture was then filtered through Celite
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated in vacuo to a semi-solid

Sources & evidence

ORD record
ord-d267cc27b327443b80ff30879dfb34a2
Source dataset
uspto-grants-2000_06
Patent number
US06075151

Reaction notes

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