2-Fluoroethanol → N-(3-chloro-4-fluorophenyl)-2-(2-fluoroethoxy)-4-methylamino-5-nitro-benzamide

HRID 410122Notes

Reaction equation

HRID 410122 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[F:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:32])[C:20]2[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[C:23]([NH:29][CH3:30])=[CH:22][C:21]=2F)=[CH:14][C:13]=1[Cl:33].[F:34][CH2:35][CH2:36][OH:37]>C1COCC1>[Cl:33][C:13]1[CH:14]=[C:15]([NH:18][C:19](=[O:32])[C:20]2[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[C:23]([NH:29][CH3:30])=[CH:22][C:21]=2[O:37][CH2:36][CH2:35][F:34])[CH:16]=[CH:17][C:12]=1[F:11]

Participants

5

Reactant 3

HCID 97372-Fluoroethanol2×HCID 3251421Potassium bis(trimethylsilyl)amide2×HCID 67957648N-(4-Fluoro-3-chloro-phenyl)-2-fluoro-4-methylamino-5-nitro-benzoic acid amide

Product 1

HCID 86669642N-(3-chloro-4-fluorophenyl)-2-(2-fluoroethoxy)-4-methylamino-5-nitro-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

KHMDS (0.320 g, 1.60 mmol) is added to an ice-cooled mixture of N-(4-fluoro-3-chloro-phenyl)-2-fluoro-4-methylamino-5-nitro-benzoic acid amide (500 mg, 1.46 mmol), 2-fluoroethanol (0.129 ml, 2.19 mmol) and 30 ml THF. After 30 min the temperature is raised to 60° C. for 4.5 h, then it is stirred at rt overnight. Additional 2-fluoroethanol (0.129 ml, 2.19 mmol) and KHMDS (0.160 g, 0.80 mmol) are added and it is stirred for 4.5 h at 60° C. Then the mixture is diluted with satd. aq. NaHCO3-solution and the precipitate is filtered off, washed with water and dried.

Workup

  1. temperaturecooled
  2. stirringit is stirred for 4.5 h at 60° C
  3. additionThen the mixture is diluted with satd
  4. filtrationaq. NaHCO3-solution and the precipitate is filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-4a986c4676314b6fb8251efc18976a08
Source dataset
uspto-grants-2014_06
Patent number
US08759537B2

Reaction notes

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