Triethylamine → HCID 10144265, compound

HRID 2289688Notes

Reaction equation

HRID 2289688 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].[CH:26]([C:29]1[CH:34]=[C:33]([S:35][C:36]#[N:37])[CH:32]=[C:31]([CH:38]([CH3:40])[CH3:39])[C:30]=1[O:41][S:42](=[O:45])(=[O:44])[NH2:43])([CH3:28])[CH3:27].C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C)C=O>[CH:26]([C:29]1[CH:34]=[C:33]([S:35][C:36]#[N:37])[CH:32]=[C:31]([CH:38]([CH3:40])[CH3:39])[C:30]=1[O:41][S:42](=[O:44])(=[O:45])[NH:43][C:23](=[O:24])[CH2:22][C:11]1[C:10]([CH:7]([CH3:8])[CH3:9])=[CH:15][C:14]([CH:16]([CH3:18])[CH3:17])=[CH:13][C:12]=1[CH:19]([CH3:21])[CH3:20])([CH3:27])[CH3:28]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 105156412,4,6-Triisopropylphenylacetic acidHCID 54144007HCID 54144007, compound

Product 1

HCID 10144265HCID 10144265, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

Oxalyl chloride (0.6 mL, 6.9 mmol) was added dropwise to a solution of 2,4,6-triisopropylphenyl acetic acid (1.52 g, 5.8 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 redissolved in 150 mL dichloromethane. Sulfamic acid 2,6-diisopropyl-4-thiocyanato-phenyl ester (1.70 g, 5.8 mmol) and triethylamine (2.0 mL) were added, and the resulting mixture was stirred for 2 hours. Washed with 1M HCl, dried the organic layer over magnesium sulfate, filtered, and concentrated to give 2.24 g of [(2,4,6-triisopropyl-phenyl)-acetyl]-sulfamic acid 2,6-diisopropyl-4-thiocyanato-phenyl ester as a white solid; mp 164-165° C.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was redissolved in 150 mL dichloromethane
  3. stirringthe resulting mixture was stirred for 2 hours
  4. washWashed with 1M HCl
  5. dry with materialdried the organic layer over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f06acbcbb1d3460c81374aedaece22a5
Source dataset
uspto-grants-2000_07
Patent number
US06093744

Reaction notes

Loading…