2,4,5-Trichlorophenol → HCID 67799125, compound

HRID 1609248Notes

Reaction equation

HRID 1609248 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][N:17]1[C:25]2[C:20](=[CH:21][C:22]([N+:26]([O-:28])=[O:27])=[CH:23][CH:24]=2)[C:19]([CH2:29][C:30]2[CH:38]=[CH:37][C:33]([C:34]([OH:36])=[O:35])=[CH:32][C:31]=2[O:39][CH3:40])=[CH:18]1.[Cl:41][C:42]1[CH:47]=[C:46]([Cl:48])[C:45]([Cl:49])=[CH:44][C:43]=1O>CN(C)C1C=CN=CC=1.O1CCCC1>[Cl:41][C:42]1[CH:47]=[C:46]([Cl:48])[C:45]([Cl:49])=[CH:44][C:43]=1[O:35][C:34](=[O:36])[C:33]1[CH:37]=[CH:38][C:30]([CH2:29][C:19]2[C:20]3[C:25](=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=3)[N:17]([CH3:16])[CH:18]=2)=[C:31]([O:39][CH3:40])[CH:32]=1

Participants

6

Reactant 3

HCID 72712,4,5-TrichlorophenolHCID 10868DicyclohexylcarbodiimideHCID 114732643-Methoxy-4-[(1-methyl-5-nitro-1H-indol-3-yl)methyl]benzoic acid

Product 1

HCID 67799125HCID 67799125, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Process Step a2): 1.66 g of dicyclohexylcarbodiimide are added at room temperature, with stirring and in a nitrogen atmosphere, to a mixture of 2.38 of 4-(1-methyl-5-nitroindol -3-ylmethyl)-3-methoxybenzoic acid [Example 1, Process Step a1)], 1.48 g of 2,4,5-trichlorophenol and 1.0 g of 4-dimethylaminopyridine in 140 ml of tetrahydrofuran. The reaction mixture is stirred at room temperature for 15 hours and filtered. The filtrate is concentrated by evaporation in vacuo at 50° and the residue is dissolved in 400 ml of chloroform, with heating. The organic phase is washed at room temperature with 50 ml of 2N hydrochloric acid and 50 ml of water and dried over magnesium sulfate, and the solution is concentrated to dryness at 40° under 11 torr. The residue is chromatographed on 350 g of silica gel (eluant: dichloromethane). The 3-methoxy-4-(1-methyl-5-nitroindol -3-ylmethyl)-benzoic acid 2.4,5 -trichlorophenyl ester obtained in that manner is suspended in 50 ml of ether and isolated by filtration. Yield 67%. Yellow crystals of m.p. 235°-236°.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated by evaporation in vacuo at 50°
  3. dissolutionthe residue is dissolved in 400 ml of chloroform
  4. temperaturewith heating
  5. washThe organic phase is washed at room temperature with 50 ml of 2N hydrochloric acid and 50 ml of water
  6. dry with materialdried over magnesium sulfate
  7. concentrationthe solution is concentrated to dryness at 40° under 11 torr
  8. customThe residue is chromatographed on 350 g of silica gel (eluant: dichloromethane)

Sources & evidence

ORD record
ord-3fb67c013c10458784a8e01cc2c8d7a9
Source dataset
uspto-grants-1995_03
Patent number
US05399714

Reaction notes

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