Triethylamine → HCID 9956174, compound

HRID 1740806Notes

Reaction equation

HRID 1740806 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])[N:8]([C:16](=[O:27])[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([OH:26])=O)[CH:19]=1)[CH2:7][CH2:6]2.C(Cl)(=O)C(Cl)=O.[CH3:34][N:35]([CH3:39])[CH2:36][CH2:37][NH2:38].C(N(CC)CC)C.[OH-].[Na+]>ClCCl.CN(C)C=O.O1CCCC1.O>[CH3:1][S:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])[N:8]([C:16](=[O:27])[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24](=[O:26])[NH:38][CH2:37][CH2:36][N:35]([CH3:39])[CH3:34])[CH:19]=1)[CH2:7][CH2:6]2

Participants

10

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 66053N,N-DimethylethylenediamineHCID 180051075-Methylthio-6-trifluoromethyl-1-(3-carboxy Phenyl Carbamoyl)indoline

Product 1

HCID 9956174HCID 9956174, compoundYield 45%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-methylthio-6-trifluoromethyl-1-(3-carboxy phenyl carbamoyl) indoline (0.5 g, 1.26mmol) in dichloromethane (20 ml) was added oxalyl chloride (0.3 ml, 2.52 mmol) and dimethylformamide (3 drops). After effervescing had subsided the reaction mixture was evaporated to dryness under reduced pressure. It was then dissolved in tetrahydrofuran (30 ml) and added to a solution of N,N-dimethylethylenediamine (0.405 g, 6.33mmol) and triethylamine (0.2 ml, 1.4 mmol) in tetrahydrofuran at 0° C. After 2 hours the reaction mixture was basified with 5M NaOH and water was added forming a white precipitate. This was filtered and dried to give the product a white solid (0.25 g, 45%), m.p. 91-93° C.

Workup

  1. customwas evaporated to dryness under reduced pressure
  2. dissolutionIt was then dissolved in tetrahydrofuran (30 ml)
  3. additionwas added
  4. customforming a white precipitate
  5. filtrationThis was filtered
  6. customdried

Sources & evidence

ORD record
ord-f8280e4dd96b47f9a1c79f68bf4aa884
Source dataset
uspto-grants-1999_10
Patent number
US05972937

Reaction notes

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