Benzoyl chloride → HCID 19855561, compound

HRID 1649992Notes

Reaction equation

HRID 1649992 reaction equation
C[C@@H]1O[C@@H](O[C@@H]2C[C@:17]3(O)[C@@:12](CO)([C@H:13]4[C@H:26]([OH:27])C[C@@]5(C)[C@](O)(CC[C@@H]5C5COC(=O)C=5)[C@@H:14]4[CH2:15][CH2:16]3)[C@H](O)C2)[C@H](O)[C@H](O)[C@H]1O.[OH-].[Na+].Cl.[CH3:45][C:46]1[CH:51]=[CH:50][CH:49]=[C:48]([CH3:52])[C:47]=1[NH:53][CH2:54][CH:55]([OH:57])[CH3:56].C(Cl)(=O)C1C=CC=CC=1>C1C=CC=CC=1>[CH3:52][C:48]1[CH:49]=[CH:50][CH:51]=[C:46]([CH3:45])[C:47]=1[N:53]([CH2:54][CH:55]([OH:57])[CH3:56])[C:26](=[O:27])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:12]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 439501OuabainHCID 19855578HCID 19855578, compound

Product 1

HCID 19855561HCID 19855561, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

100 ml of a 2 n aqueous sodium hydroxide solution are added dropwise, under ice cooling and vigorous stirring, to a suspension of 21.6 g (0.1 moles) of 1-(2,6-dimethylphenyl-amino)-2-propanol hydrochloride in 100 ml of benzene, and then 12.2 ml (14.6 g, 0.1 moles) of benzoyl chloride are dropped into the mixture at room temperature. The resulting mixture is stirred at room temperature for 5 hours and allowed to stand overnight. The aqueous phase is separated, the benzene phase is washed twice with 50 ml of water, twice with 50 ml of a 1 n hydrochloric acid solution and then thrice with 50 ml of water, each, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. 26.6 g (94%) of 1-[N-(2,6-dimethylphenyl)-benzamido]-2-propanol are obtained as a white, crystalline substance; m.p.: 121°-122° C.

Workup

  1. waitto stand overnight
  2. customThe aqueous phase is separated
  3. washthe benzene phase is washed twice with 50 ml of water, twice with 50 ml of a 1 n hydrochloric acid solution
  4. dry with materialeach, dried over anhydrous magnesium sulfate
  5. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-232f52952577431a9086a63a0eb945f2
Source dataset
uspto-grants-1990_05
Patent number
US04922021

Reaction notes

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