Hydrochloric Acid → HCID 10805454, compound

HRID 1586228Notes

Reaction equation

HRID 1586228 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]([C:9]1[CH:10]=[C:11]([CH:15]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=2)[CH2:16][C:17]([OH:19])=O)[CH:12]=[CH:13][CH:14]=1)#[N:8].[CH3:30][NH2:31].Cl>C(Cl)Cl.O.C(OCC)(=O)C>[C:28]([C:25]1[CH:24]=[CH:23][C:22]([CH2:21][CH2:20][CH:15]([C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([C:7]#[N:8])[CH:10]=2)[CH2:16][C:17]([NH:31][CH3:30])=[O:19])=[CH:27][CH:26]=1)#[N:29]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 65578Oxalyl chlorideHCID 10709631HCID 10709631, compound

Product 1

HCID 10805454HCID 10805454, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Part A. Oxalyl chloride was added to a solution of 3-(3-cyanophenyl)-5-(4-cyanophenyl)pentanoic acid (0.25 gm, 0.82 mmol) in 10 mLs methylene chloride under a nitrogen atmosphere at ambient temperature. The reaction was stirred for 2 hrs and was concentrated in vacuo to give a semi solid residue. The residue was taken up in 5 mLs methylene chloride and 40% methyl amine in water (5 mLs) was added. The reaction was stirred vigorously for 2 hrs and then was partioned between 1N HCl and ethyl acetate. The organic layer was washed with water, brine dried over magnesium sulfate and concentrated to give the crude product as a semisolid. The residue was purified by flash chromatography on silica gel (100 mLs) eluting methylene chloride:ethyl acetate (v:v, 80:20) to give 4-(cyano)-beta-(3-cyanophenyl)-N-methylbenzenepentanamide as a semisolid 0.120 gm (46%) MS 335(M+NH4) 1H NMR (CDCl3): 7.6-7.4(m, 6H), 7.17(d, 2H), 5.3(m, 1H), 3.27(m, 1H), 2.67(d, 2H), 2.55-2.35(m, 4H), 2.07(m, 1H), 1.95(m, 1H).

Workup

  1. concentrationwas concentrated in vacuo
  2. customto give a semi solid residue
  3. stirringThe reaction was stirred vigorously for 2 hrs
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give the crude product as a semisolid
  8. customThe residue was purified by flash chromatography on silica gel (100 mLs)
  9. washeluting methylene chloride

Sources & evidence

ORD record
ord-0e0a9e40a4be48d88b429e7f7b7c246b
Source dataset
uspto-grants-1999_08
Patent number
US05942544

Reaction notes

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