Triethylamine → HCID 10255988, compound

HRID 1647577Notes

Reaction equation

HRID 1647577 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:33])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O: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][CH2:31][CH3:32])[CH:13]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[Br-:46].[Li+]>O1CCCC1>[Br:46][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:33])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O: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][CH2:31][CH3:32])[CH:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 82050Lithium BromideHCID 10004072HCID 10004072, compound

Product 1

HCID 10255988HCID 10255988, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4 g of N-[2-(hydroxymethyl)phenyl]-3-(tetradecyloxy)benzeneacetamide in 75 ml of tetrahydrofuran is added 1.19 g of triethylamine and 1.34 g of methanesulfonyl chloride, followed by stirring at room temperature for 1.5 hours. Added 7.66 g of lithium bromide with stirring continued for an additional 2.5 hours. The solvent is evaporated and the residue partitioned between chloroform and saturated sodium bicarbonate. The organic layer is dried and evaporated to a residue which is crystallized from hexane to give 2.6 g of the desired product as a white solid, m.p. 103°-106° C.

Workup

  1. stirringwith stirring
  2. waitcontinued for an additional 2.5 hours
  3. customThe solvent is evaporated
  4. customthe residue partitioned between chloroform and saturated sodium bicarbonate
  5. customThe organic layer is dried
  6. customevaporated to a residue which
  7. customis crystallized from hexane

Sources & evidence

ORD record
ord-538257a16e9b413c84c92dbbd06f4b70
Source dataset
uspto-grants-1995_07
Patent number
US05432189

Reaction notes

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