Acetic Acid → 3-fluoro-4-[5-(4-methylthiobenzoyl)-1,4-dimethyl-1H-pyrrol-2-ylmethyl]aniline

HRID 369414Notes

Reaction equation

HRID 369414 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[N:11]([CH3:25])[C:12]([C:16](=O)[C:17]2[CH:22]=[CH:21]C(Cl)=[CH:19][CH:18]=2)=[C:13]([CH3:15])[CH:14]=1)[NH2:5].C[S-:27].[Na+].[C:29](O)(=O)[CH3:30]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[N:11]([CH3:25])[C:12]([C:16](=[S:27])[C:17]2[CH:22]=[CH:21][C:29]([CH3:30])=[CH:19][CH:18]=2)=[C:13]([CH3:15])[CH:14]=1)[NH2:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4378561Sodium methanethiolateHCID 538537063-Fluoro-4-[5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-ylmethyl]aniline

Product 1

HCID 867545043-fluoro-4-[5-(4-methylthiobenzoyl)-1,4-dimethyl-1H-pyrrol-2-ylmethyl]anilineYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Fluoro-4-[5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-ylmethyl]aniline (2.0 g, 5.6 mmol) was dissolved in degassed DMF. Sodium thiomethoxide (1.5 g, 22.4 mmol) was added and the mixture stirred at room temperature under argon for 24 h. The reaction was poured into ice-water, acidified with acetic acid to pH 3 and extracted with ethyl acetate. The organic extracts were washed with water, and brine, and dried over magnesium sulfate. The solvent was removed in vacuo and the crude product was purified on a silica gel column (methylene chloride-methanol-acetone, 96:2:2) to give 3-fluoro-4-[5-(4-methylthiobenzoyl)-1,4-dimethyl-1H-pyrrol-2-ylmethyl]aniline (1.13 g, 55%) as a solid, mp 199.1-199.7° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts were washed with water, and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed in vacuo
  5. customthe crude product was purified on a silica gel column (methylene chloride-methanol-acetone, 96:2:2)

Sources & evidence

ORD record
ord-afce90b0699c4d7d95b32afa0bef3008
Source dataset
uspto-grants-2000_10
Patent number
US06136844

Reaction notes

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