Methyl iodide → Methyl 4-[15-(trifluoromethyl)pentadecylamino]benzoate

HRID 1105897Notes

Reaction equation

HRID 1105897 reaction equation
[F:1][C:2]([F:29])([F:28])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1.[H-].[Na+].[CH3:32]I>CN(C)P(N(C)C)(N(C)C)=O>[F:1][C:2]([F:28])([F:29])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([O:25][CH3:32])=[O:24])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 128316104-[15-(Trifluoromethyl)pentadecylamino]benzoic acid

Product 1

HCID 20549341Methyl 4-[15-(trifluoromethyl)pentadecylamino]benzoate

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent2×

Procedure

A solution of 7.20 g. of 4-[15-(trifluoromethyl)pentadecylamino]benzoic acid in 25 ml. of hexamethylphosphoramide is added to a stirred mixture of 0.800 g. of sodium hydride (57% in mineral oil) and 25 ml. of hexamethylphosphoramide. The solution which forms after one hour is treated with 11.0 g. of methyl iodide and is then stirred at 25° C. for 18 hours. Dilution with water followed by filtration affords a white solid which is crystallized from ethanol to yield the product as a white solid.

Workup

  1. additionis treated with 11.0 g
  2. filtrationDilution with water followed by filtration
  3. customaffords a white solid which
  4. customis crystallized from ethanol

Sources & evidence

ORD record
ord-22189617778d4e81b6c6c5fdf760ae52
Source dataset
uspto-grants-1982_01
Patent number
US04310545

Reaction notes

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