Triethylamine → N-[3-(Bromomethyl)phenyl]-4-(tetradecyloxy)benzamide

HRID 483561

Reaction equation

HRID 483561 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:32])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:13][CH:12]=2)[CH:6]=[CH:7][CH:8]=1.CS(Cl)(=O)=O.C(N(CC)CC)C.[Br-:45].[Li+]>O1CCCC1.O>[Br:45][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:32])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:13][CH:12]=2)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 82050Lithium BromideHCID 10003333N-[3-(Hydroxymethyl)phenyl]-4-(tetradecyloxy)benzamide

Product 1

HCID 11755784N-[3-(Bromomethyl)phenyl]-4-(tetradecyloxy)benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[3-(hydroxymethyl)phenyl]-4-(tetradecyloxy)benzamide and 3.47 g of methanesulfonyl chloride in 200 ml of tetrahydrofuran is added 3.07 g of triethylamine followed by stirring at ambient temperature for 2 hours. Also added is 21.93 g of lithium bromide followed by stirring at ambient temperature for an additional 3 hours. The mixture is poured into water and extracted with ether. The organic layer is washed with a mixture of brine and saturated sodium bicarbonate then dried. The solvent is removed under vacuum and the residue crystallized from carbon tetrachloride:hexanes to give the desired product as a white solid, m.p. 116°-118° C.

Workup

  1. additionAlso added
  2. stirringby stirring at ambient temperature for an additional 3 hours
  3. extractionextracted with ether
  4. washThe organic layer is washed with a mixture of brine and saturated sodium bicarbonate
  5. customthen dried
  6. customThe solvent is removed under vacuum
  7. customthe residue crystallized from carbon tetrachloride

Sources & evidence

ORD record
ord-968b08bd862b4f7db8dbc2772a52cf2a
Source dataset
uspto-grants-1993_07
Patent number
US05225425

Linked notes

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