Methyl iodide → Methyl 4-[14-(trimethylsilyl)tetradecylamino]benzoate

HRID 652024Notes

Reaction equation

HRID 652024 reaction equation
[CH3:1][Si:2]([CH3:28])([CH3:27])[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][NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1.[H-].[Na+].[CH3:31]I>CN(C)P(N(C)C)(N(C)C)=O>[CH3:28][Si:2]([CH3:1])([CH3:27])[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][NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH3:31])=[O:23])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 138848624-[14-(Trimethylsilyl)tetradecylamino)benzoic acid

Product 1

HCID 20198250Methyl 4-[14-(trimethylsilyl)tetradecylamino]benzoate

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent2×

Procedure

A solution of 7.0 g. of 4-[14-(trimethylsilyl)tetradecylamino)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-4a1debefb365470e866652f171b5e60a
Source dataset
uspto-grants-1987_06
Patent number
US04670421

Reaction notes

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