Methanol → HCID 10224082, compound

HRID 1796501Notes

Reaction equation

HRID 1796501 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=S)SC)=[CH:6][CH:5]=1)[CH3:2].[NH2:15][C:16]1[CH:17]=[C:18]([CH:26]=[CH:27][C:28]=1[NH:29][CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])[C:19]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=[O:20].CO>CN(C=O)C.C(Cl)Cl.[Hg]=O>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:29]([CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])[C:28]3[CH:27]=[CH:26][C:18]([C:19]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=[O:20])=[CH:17][C:16]=3[N:15]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

7

Reactant 3

HCID 887MethanolHCID 3032585Carbanilic acid, dithio-p-ethoxy-, methyl esterHCID 22181315HCID 22181315, compound

Product 1

HCID 10224082HCID 10224082, compoundYield 56.6%

Reagents, catalysts & solvents 3

HCID 30856Mercuric oxideCatalyst2×HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 4-ethoxyphenyldithiocarbamate (0.0274 g, 0.121 mmol) in DMF (0.2 mL) was added to a mixture of 3-amino-N,N-diethyl-4-(isopentylamino)benzamide (0.0334 g, 0.120 mmol) and red mercury(II) oxide (0.0261 g, 0.121 mmol) in DMF (0.2 mL). The resulting suspension was stirred vigorously for 5.5 h, and an additional portion of red mercury(II) oxide (0.0130 g, 0.0600 mmol) was added. After stirring an additional 16 h, the reaction was diluted with 9:1 CH2Cl2:MeOH, loaded onto a small plug of silica gel, and eluted with the same solvent system. The eluant was concentrated, and the residue was purified by reverse phase HPLC (gradient 20–70% CH3CN in H2O) to provide the title compound (0.0287 g, 45%) as its TFA salt. This material was lyophilized from H2O/dioxane to produce a white solid. 1H-NMR (CD3OD): δ 7.60 (d, J=8.4 Hz, 1H), 7.44–7.38 (2 overlapping d; 3H), 7.35 (s, 1H), 7.11 (d, J=9.2 Hz, 2H), 4.32 (br t, J=7.2 Hz, 2H), 4.12 (q, J=7.6 Hz, 2H), 3.56 (br s, 2H), 3.32 (br s, 2H), 1.85–1.76 (br m, 3H), 1.43 (t, 7.6 Hz, 3H), 1.25 (br s, 3H), 1.14 (br s, 3H), 1.08 (d, J=6.4 Hz, 6H). 13C-NMR(CD3OD): δ 172.51, 160.57, 151.15, 134.20, 132.87, 130.29, 128.70, 128.44, 123.46, 117.18, 111.54, 111.23, 65.02, 45.07, 43.16, 41.13, 37.49, 27.26, 22.76, 15.07, 14.35, 13.07. Anal. Calcd for MS (ESI) (M+H)+=423.

Workup

  1. stirringAfter stirring an additional 16 h
  2. washeluted with the same solvent system
  3. concentrationThe eluant was concentrated
  4. customthe residue was purified by reverse phase HPLC (gradient 20–70% CH3CN in H2O)

Sources & evidence

ORD record
ord-fe108441e3494e4fa717b8b6076fb25f
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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