Dimethylformamide → HCID 178522878, compound

HRID 2289946Notes

Reaction equation

HRID 2289946 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:20]([F:23])([F:22])[F:21])=[C:9]([S:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:24]([OH:26])=O.CN(C)C=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:44][C:45]1[CH:52]=[CH:51][C:48]([CH2:49][NH2:50])=[CH:47][CH:46]=1>O>[Cl:44][C:45]1[CH:52]=[CH:51][C:48]([CH2:49][NH:50][C:24]([C:3]2[CH:4]=[N:5][C:6]3[C:11]([C:2]=2[OH:1])=[CH:10][C:9]([S:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:8]([C:20]([F:21])([F:22])[F:23])[CH:7]=3)=[O:26])=[CH:47][CH:46]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 660364-ChlorobenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 178524719HCID 178524719, compound

Product 1

HCID 178522878HCID 178522878, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
37.5 °C

Procedure

A mixture of 0.15 g of 4-hydroxy-6-[(phenylmethyl)thio]-7-(trifluoromethyl)-3-quinolinecarboxylic acid and 1.2 mL of dimethylformamide is treated with 0.075 g of carbonyldiimidazole. The mixture is stirred 20 h at 35-40° C. The solution is cooled to 25° C. and it is treated with 0.075 mL of distilled water and then it is stirred for 10 min. The solution is treated with 0.053 mL of 4-chlorobenzylamine and it is stirred for 18 h. The mixture is diluted with 1.0 mL of distilled water and then it is decanted from a dark, oily precipitate. This precipitate is treated with 1 mL of glacial acetic acid and the mixture is shaken for 5 min. The solid which formed is collected by filtration and it is washed with a few mL of 50% aqueous acetic acid. The solid is dried in a stream of air to give 48 mg of the title compound.

Workup

  1. temperatureThe solution is cooled to 25° C.
  2. stirringit is stirred for 10 min
  3. stirringis stirred for 18 h
  4. customit is decanted from a dark, oily precipitate
  5. additionThis precipitate is treated with 1 mL of glacial acetic acid
  6. stirringthe mixture is shaken for 5 min
  7. customThe solid which formed
  8. filtrationis collected by filtration and it
  9. washis washed with a few mL of 50% aqueous acetic acid
  10. customThe solid is dried in a stream of air

Sources & evidence

ORD record
ord-d487ed14ce334527b04f8c59cc1ef805
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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