Thionyl Chloride → HCID 86595906, compound

HRID 1296773Notes

Reaction equation

HRID 1296773 reaction equation
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([O:17][CH3:18])[C:15]=1[CH3:16])[C:10]([OH:12])=O.[NH2:19][CH2:20][C:21]1[CH:35]=[CH:34][C:24]([CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:23][C:22]=1[N+:36]([O-:38])=[O:37]>CN(C=O)C.C1C=CC=CC=1.ClCCl.C(OCC)(=O)C>[CH3:18][O:17][C:14]1[CH:13]=[C:9]([CH:8]=[C:7]([O:6][CH3:5])[C:15]=1[CH3:16])[C:10]([NH:19][CH2:20][C:21]1[CH:35]=[CH:34][C:24]([CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:23][C:22]=1[N+:36]([O-:38])=[O:37])=[O:12]

Participants

8

Reactant 3

HCID 24386Thionyl ChlorideHCID 37644863,5-Dimethoxy-4-methylbenzoic acidHCID 86595905HCID 86595905, compound

Product 1

HCID 86595906HCID 86595906, compoundYield 100%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

DMF (2 drops) and thionyl chloride (0.080 mL, 1.1 mmol) were sequentially added to a suspension of 3,5-dimethoxy-4-methyl benzoic acid (0.0995 g, 0.507 mmol) in benzene (2 mL). The reaction mixture was heated at reflux for 2 h, and then concentrated. The residue was dissolved in dichloromethane (1 mL) and then added dropwise to a solution of compound 65c (0.144 g, 0.512 mmol) and TEA (0.2 mL, 1.4 mmol) in dichloromethane (1 mL). The reaction mixture was stirred overnight at rt. The mixture was diluted with ethyl acetate and washed with 0.1 N HCl (2×) and saturated sodium bicarbonate solution, dried, and concentrated to give compound 65d (0.233 g, 100%) as a yellow solid ESI-MS m/e 460.4 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in dichloromethane (1 mL)
  5. washwashed with 0.1 N HCl (2×) and saturated sodium bicarbonate solution
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8b8681b5c8754aa8a78b1315cb74837f
Source dataset
uspto-grants-2007_07
Patent number
US07247654B2

Reaction notes

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