Triethylamine → HCID 10007971, compound

HRID 1647605Notes

Reaction equation

HRID 1647605 reaction equation
[CH2:1]([O:17][C:18]1[CH:36]=[CH:35][C:21]([O:22][CH2:23][C:24]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH2:33]O)=[O:25])=[CH:20][CH:19]=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][CH2:14][CH2:15][CH3:16].CS(Cl)(=O)=O.C(N(CC)CC)C.[Br-:49].[Li+]>O1CCCC1.O>[Br:49][CH2:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[NH:26][C:24](=[O:25])[CH2:23][O:22][C:21]1[CH:35]=[CH:36][C:18]([O:17][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][CH2:14][CH2:15][CH3:16])=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 82050Lithium BromideHCID 9983353HCID 9983353, compound

Product 1

HCID 10007971HCID 10007971, compoundYield 50.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.5 g of 2-[4-(hexadecyloxy)phenoxy]-N-[2-(hydroxymethyl)phenyl]acetamide and 1.29 g of methanesulfonyl chloride in 60 ml of tetrahydrofuran is added 853.89 mg of triethylamine followed by stirring at room temperature for 2.5 hours. Also added is 6.11 g of lithium bromide followed by stirring at room temperature for 4 hours. The mixture is poured into water and extracted with ether. The organic layer is dried and passed through a pad of magnesium silicate. The solvent is evaporated to a residue which is crystallized from hexane to give 2.0 g of the desired product as a white solid.

Workup

  1. additionAlso added
  2. stirringby stirring at room temperature for 4 hours
  3. extractionextracted with ether
  4. customThe organic layer is dried
  5. customThe solvent is evaporated to a residue which
  6. customis crystallized from hexane

Sources & evidence

ORD record
ord-9ee3f4bbb2f141aead909dea518def52
Source dataset
uspto-grants-1995_07
Patent number
US05432189

Reaction notes

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