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

HRID 2227036Notes

Reaction equation

HRID 2227036 reaction equation
[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([NH2:25])=[O:24])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C(N([CH2:31][CH3:32])CC)C.CS(Cl)(=O)=O.[Br-:38].[Li+]>O1CCCC1>[Br:38][CH2:5][C:4]1[CH:3]=[C:2]([NH:25][C:23](=[O:24])[CH2:22][C:19]2[CH:20]=[CH:21][C:16]([O:15][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:17][CH:18]=2)[CH:1]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 82050Lithium BromideHCID 86745364HCID 86745364, compound

Product 1

HCID 10052253N-[3-(Bromomethyl)phenyl]-4-(tetradecyloxy)-benzeneacetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4.0 g of N-[3-hydroxymethyl)phenyl]-4-(tetradecyloxy)-benzeneacetamide in 100 ml of tetrahydrofuran is added 1.19 g of triethylamine followed by 1.34 g of methanesulfonyl chloride. Also added is 7.66 g of lithium bromide and continued stirring for 24 hours. The solvent is removed under vacuum and the residue is partitioned between chloroform and water followed by an additional wash of the organic layer with saturated sodium bicarbonate. The organic layer is dried and filtered through a pad of silica gel. The filtrate is evaporated to a residue which is crystallized from hexane:carbon tetrachloride to give 4.1 g of the desired product as a white powder, m.p. 116°-118° C.

Workup

  1. additionAlso added
  2. customThe solvent is removed under vacuum
  3. customthe residue is partitioned between chloroform and water
  4. washan additional wash of the organic layer with saturated sodium bicarbonate
  5. customThe organic layer is dried
  6. filtrationfiltered through a pad of silica gel
  7. customThe filtrate is evaporated to a residue which
  8. customis crystallized from hexane

Sources & evidence

ORD record
ord-b12643036663415aba7eb21d71764258
Source dataset
uspto-grants-1994_09
Patent number
US05350759

Reaction notes

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