Pyridine → HCID 10938596, compound

HRID 2294630Notes

Reaction equation

HRID 2294630 reaction equation
[CH2:1]([O:8][CH:9]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10]([OH:12])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.N1C=CC=CC=1.[F:33][C:34]([F:43])([F:42])[C:35]1[CH:36]=[C:37]([CH:39]=[CH:40][CH:41]=1)[NH2:38]>ClCCl.CN(C)C1C=CN=CC=1.O>[CH2:14]([O:13][CH:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:10]([NH:38][C:37]1[CH:39]=[CH:40][CH:41]=[C:35]([C:34]([F:33])([F:42])[F:43])[CH:36]=1)=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 73753-(Trifluoromethyl)anilineHCID 65578Oxalyl chlorideHCID 12762576HCID 12762576, compound

Product 1

HCID 10938596HCID 10938596, compoundYield 92.1%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of dibenzyloxyacetic acid (4.0 g, prepared as described in Step 2) in dichloromethane (40 ml) was cooled to 0° C. and treated dropwise with, successively, 4-N,N-dimethylformamide (100 mg) and oxalyl chloride (2.0 g). After thirty minutes, pyridine (3.52 g), 3-trifluoromethyl aniline (2.64 g) and 4-dimethylaminopyridine (100 mg) were added. The mixture was stirred at 0° C. for a further thirty minutes then allowed to warm to room temperature. After three hours, it was poured into water, extracted with ethyl acetate and the extracts washed successively with dilute hydrochloric acid, water, aqueous sodium bicarbonate solution, and brine. After drying over magnesium sulphate, the extracts were evaporated under reduced pressure to give the title compound (5.62 g) as an orange gum, sufficiently pure to be used in Step 4.

Workup

  1. waitAfter thirty minutes
  2. temperatureto warm to room temperature
  3. extractionextracted with ethyl acetate
  4. washthe extracts washed successively with dilute hydrochloric acid, water, aqueous sodium bicarbonate solution, and brine
  5. dry with materialAfter drying over magnesium sulphate
  6. customthe extracts were evaporated under reduced pressure

Sources & evidence

ORD record
ord-93446895555242a58b6370abf112807e
Source dataset
uspto-grants-1997_11
Patent number
US05688962

Reaction notes

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