4-Chlorophenylacetyl chloride → HCID 10094749, compound

HRID 602520Notes

Reaction equation

HRID 602520 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:10][C:11]2[S:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[CH3:9])[CH:5]=[CH:4][C:3]=1[NH2:17].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26](Cl)=[O:27])=[CH:21][CH:20]=1.C(=O)(O)[O-].[Na+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:10][C:11]2[S:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[CH3:9])[CH:5]=[CH:4][C:3]=1[NH:17][C:26](=[O:27])[CH2:25][C:22]1[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 906924-Chlorophenylacetyl chlorideHCID 516892Sodium BicarbonateHCID 67267820HCID 67267820, compound

Product 1

HCID 10094749HCID 10094749, compoundYield 16.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

2-Chloro-N(4)-(5-chloro-thiophen-2-ylmethyl)-N(4)-methyl-benzene-1,4-diamine (100 mg) was added to a solution of 4-chlorophenylacetyl chloride (69 mg) in dry acetonitrile (2 mL) in a rubber-capped glass vial. The reaction mixture was heated in a microwave device to 150° C. for 15 minutes. The reaction mixture was poured into saturated aqueous sodium bicarbonate (5 mL) and extracted with ethyl acetate (5 mL). The organic phase was washed with water (5 mL) and brine (5 mL), dried over sodium sulfate, filtered, and evaporated to dryness. The crude product was purified by flash chromatography (heptane/ethyl acetate, gradient) to furnish 25.2 mg title compound. Yield: 16%.

Workup

  1. extractionextracted with ethyl acetate (5 mL)
  2. washThe organic phase was washed with water (5 mL) and brine (5 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product was purified by flash chromatography (heptane/ethyl acetate, gradient)

Sources & evidence

ORD record
ord-0f40389350ba4282a028e4fee81e1067
Source dataset
uspto-grants-2011_03
Patent number
US07906537B2

Reaction notes

Loading…