Triethylamine → HCID 10187839, compound

HRID 2289678Notes

Reaction equation

HRID 2289678 reaction equation
C(Cl)(=O)C(Cl)=O.[CH:7]([C:10]1[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[CH:13]=[C:12]([CH:19]([CH3:21])[CH3:20])[C:11]=1[CH2:22][C:23](O)=[O:24])([CH3:9])[CH3:8].[CH3:26][O:27][C:28](=[O:46])[C:29]1[CH:34]=[C:33]([CH:35]([CH3:37])[CH3:36])[C:32]([O:38][S:39](=[O:42])(=[O:41])[NH2:40])=[C:31]([CH:43]([CH3:45])[CH3:44])[CH:30]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C)C=O>[CH3:26][O:27][C:28](=[O:46])[C:29]1[CH:30]=[C:31]([CH:43]([CH3:45])[CH3:44])[C:32]([O:38][S:39](=[O:41])(=[O:42])[NH:40][C:23](=[O:24])[CH2:22][C:11]2[C:10]([CH:7]([CH3:8])[CH3:9])=[CH:15][C:14]([CH:16]([CH3:18])[CH3:17])=[CH:13][C:12]=2[CH:19]([CH3:21])[CH3:20])=[C:33]([CH:35]([CH3:37])[CH3:36])[CH:34]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 105156412,4,6-Triisopropylphenylacetic acidHCID 541866693,5-Bis(1-methylethyl)-4-(sulfamoyloxy)benzoic acid methyl ester

Product 1

HCID 10187839HCID 10187839, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

Oxalyl chloride (1.12 mL, 12.8 mmol) was added dropwise to a solution of 2,4,6-triisopropylphenyl acetic acid (3.05 g, 11.6 mmol) in 150 mL toluene with 4 drops of N,N-dimethylformamide as a catalyst. The resulting solution was stirred overnight and then concentrated in vacuo. The residue was re-dissolved in 150 mL dichloromethane. 3,5-Bis(1-methylethyl)-4-(sulfamoyloxy)benzoic acid methyl ester (3.48 g, 11.6 mmol) and triethylamine (4.0 mL) were added and the resulting mixture was stirred for 2 hours. Washed with 1 M HCl, dried the organic layer over magnesium sulfate, filtered, and concentrated to give an off-white foam. Recrystallized (hexanes) to give 5.21 g of the title compound as a white solid; mp 144-146° C.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was re-dissolved in 150 mL dichloromethane
  3. stirringthe resulting mixture was stirred for 2 hours
  4. washWashed with 1 M HCl
  5. dry with materialdried the organic layer over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give an off-white foam
  9. customRecrystallized (hexanes)

Sources & evidence

ORD record
ord-88e057ab18374e71b0ff7d1f0090f45f
Source dataset
uspto-grants-2000_07
Patent number
US06093744

Reaction notes

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