Sodium Chloride → HCID 10459203, compound

HRID 484585Notes

Reaction equation

HRID 484585 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:33])[CH2:11][C:12]2[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]=2)[CH:6]=[CH:7][CH:8]=1.CS(Cl)(=O)=O.[Br-:39].[Li+].[Cl-].[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.C(N(CC)CC)C>[Br:39][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:33])[CH2:11][C:12]2[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]=2)[CH:6]=[CH:7][CH:8]=1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 31297Methanesulfonyl chlorideHCID 82050Lithium BromideHCID 516892Sodium BicarbonateHCID 9981372HCID 9981372, compound

Product 1

HCID 10459203HCID 10459203, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 3.3 g of N-[3-(hydroxymethyl)phenyl]-3-(tetradecyloxy)benzeneacetamide in 60 ml of tetrahydrofuran is added 1.11 g of methanesulfonyl chloride and 978.95 mg of triethylamine followed by stirring at ambient temperature for 2 hours. Added 6.32 g of lithium bromide and stirred for an additional 2.5 hours. The reaction is poured into a mixture of saturated sodium chloride and saturated sodium bicarbonate then extracted with ether. The organic layer is dried and evaporated to give the desired product as a white solid, m.p. 104°-106° C.

Workup

  1. stirringstirred for an additional 2.5 hours
  2. extractionthen extracted with ether
  3. customThe organic layer is dried
  4. customevaporated

Sources & evidence

ORD record
ord-faa76f19c80d4cbd95bf96a101f7e453
Source dataset
uspto-grants-1993_07
Patent number
US05231182

Reaction notes

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