Triethylamine → [(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-cyano-2,6-diisopropyl-phenyl ester

HRID 2289689Notes

Reaction equation

HRID 2289689 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]([OH:25])=O)([CH3:9])[CH3:8].[S:26](=[O:44])(=[O:43])([O:28][C:29]1[C:34]([CH:35]([CH3:37])[CH3:36])=[CH:33][C:32]([C:38]#[N:39])=[CH:31][C:30]=1[CH:40]([CH3:42])[CH3:41])[NH2:27].C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C)C=O>[C:38]([C:32]1[CH:31]=[C:30]([CH:40]([CH3:42])[CH3:41])[C:29]([O:28][S:26](=[O:43])(=[O:44])[NH:27][C:23](=[O:25])[CH2:22][C:11]2[C:10]([CH:7]([CH3:8])[CH3:9])=[CH:15][C:14]([CH:16]([CH3:17])[CH3:18])=[CH:13][C:12]=2[CH:19]([CH3:21])[CH3:20])=[C:34]([CH:35]([CH3:37])[CH3:36])[CH:33]=1)#[N:39]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 105156412,4,6-Triisopropylphenylacetic acidHCID 186988442,6-Bis(l-methylethyl)-4-cyanophenyl sulfamate

Product 1

HCID 10165237[(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-cyano-2,6-diisopropyl-phenyl esterYield 45.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

Oxalyl chloride (0.48 mL, 5.5 mmol) was added dropwise to a solution of 2,4,6-triisopropylphenyl acetic acid (1.21 g, 4.6 mmol) in 100 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. 2,6-Bis(l-methylethyl)-4-cyanophenyl sulfamate (1.30 g, 4.6 mmol) and triethylamine (1.6 mL) were added, and the resulting mixture was stirred for 6 hours. Washed with 1 M HCl, dried the organic layer over magnesium sulfate, filtered, and concentrated to give an oily solid. Chromatography on silica gel (20% ethyl acetate/hexanes) gave 1.11 g of the title compound as a white solid; mp 79-84° C.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was re-dissolved in 150 mL dichloromethane
  3. stirringthe resulting mixture was stirred for 6 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 oily solid

Sources & evidence

ORD record
ord-0455928538cd4e66bad415d520922a9a
Source dataset
uspto-grants-2000_07
Patent number
US06093744

Reaction notes

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