Dimethylformamide → HCID 19011120, compound

HRID 1198296Notes

Reaction equation

HRID 1198296 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[CH:13]=[C:12]2[CH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][C:21]=1[O:29][CH3:30])=[O:8].CN(C)C=O>ClCCl>[CH3:5][O:6][C:7]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[CH:13]=[C:12]2[CH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([Cl:3])=[O:25])=[CH:22][C:21]=1[O:29][CH3:30])=[O:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 15104477HCID 15104477, compound

Product 1

HCID 19011120HCID 19011120, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of thionyl chloride (2.42 ml, 33 mmole) in dichloromethane (10 ml) was added dropwise over 5 minutes to a suspension of the product of step b) (10.59 g, 30 mmole) in dichloromethane (90 ml) containing N,N-dimethylformamide (0.2 ml), stirred at reflux under an atmosphere of nitrogen. After 2 hours, solvent was removed from the resulting yellow solution by distillation, approximately 85 ml distillate being collected. Dilution of the residue with methyl t-butyl ether was followed by stirring at 15° C. for 30 minutes prior to collection of the solid precipitate by filtration. After washing with methyl t-butyl ether (2×20 ml), 4-(5-methoxycarbonyl-1-methylindol-3-ylmethyl)-3-methoxybenzoyl chloride was obtained as an off-white solid, 10.10 g (90.6%); m.p. 147°-149° C.; NMR (250 MHz, DMSO-d6): 3.76, 3.92, 3.97 (each s, 3H, NCH3 plus OCH3 plus CO2CH3), 4.16 (s, 2H, ArCH2Ar'), 6.87 (s, 1H), 7.20 (d, 1H), 7.29 (d, 1H), 7.54 (d, 1H), 7.66 (dd, 1H), 7.92 (dd, 1H), 8.32 (d, 1H).

Workup

  1. temperatureat reflux under an atmosphere of nitrogen
  2. customsolvent was removed from the resulting yellow solution by distillation, approximately 85 ml distillate
  3. custombeing collected
  4. stirringby stirring at 15° C. for 30 minutes
  5. customto collection of the solid precipitate
  6. filtrationby filtration
  7. washAfter washing with methyl t-butyl ether (2×20 ml)

Sources & evidence

ORD record
ord-0a729a7ef71543b0aa95a2c054e8187f
Source dataset
uspto-grants-1994_01
Patent number
US05280125

Reaction notes

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