4-Chloro-2-toluidine → HCID 86754323, compound

HRID 583405Notes

Reaction equation

HRID 583405 reaction equation
C(N(CC)CC)C.[F:8][C:9]([F:41])([F:40])[C:10]1[CH:11]=[C:12]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[C:13]([N:15]([CH:17]([CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)[CH2:18][C:19](O)=[O:20])[CH3:16])=[O:14].[Cl:42][C:43]1[CH:49]=[CH:48][C:46]([NH2:47])=[C:45]([CH3:50])[CH:44]=1>C(Cl)Cl>[Cl:42][C:43]1[CH:49]=[CH:48][C:46]([NH:47][C:19](=[O:20])[CH2:18][CH:17]([N:15]([C:13](=[O:14])[C:12]2[CH:11]=[C:10]([C:9]([F:41])([F:8])[F:40])[CH:35]=[C:34]([C:36]([F:38])([F:39])[F:37])[CH:33]=2)[CH3:16])[CH2:22][C:23]2[CH:24]=[CH:25][C:30]3[C:31](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:32]=2)=[C:45]([CH3:50])[CH:44]=1

Participants

5

Reactant 3

HCID 72514-Chloro-2-toluidineHCID 8471TriethylamineHCID 54334607HCID 54334607, compound

Product 1

HCID 86754323HCID 86754323, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.055 ml (0.393 mmol) of triethylamine and 38 mg (0.0786 mmol) of 3-[N'-(3,5-bistrifluoromethyl-benzoyl)-N'-methyl-amino]-4-(2-naphthyl)-butanoic acid in 0.5 ml of methylene chloride and a solution of 33.3 mg of 1-propanephosphonic acid anhydride in 0.4 ml of methylene chloride are added in succession to 10.3 mg (0.0943 mmol) of 4-chloro-2-methylaniline and the mixture is left to stand at room temperature overnight (>16 hours). The reaction mixture is then washed with 0.5 ml of a 1N aqueous potassium carbonate solution. The aqueous phase is extracted with a further 0.8 ml of methylene chloride. The combined organic phases are concentrated by evaporation in a vacuum centrifuge. The title compound is obtained in the form of a white foam. TLC: methylene chloride/acetone (7:3) Rf =0.48.

Workup

  1. waitthe mixture is left
  2. custom(>16 hours)
  3. washThe reaction mixture is then washed with 0.5 ml of a 1N aqueous potassium carbonate solution
  4. extractionThe aqueous phase is extracted with a further 0.8 ml of methylene chloride
  5. concentrationThe combined organic phases are concentrated by evaporation in a vacuum centrifuge

Sources & evidence

ORD record
ord-1458554435764b8c9cb978bf87b027ff
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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