Triethylamine → HCID 10209327, compound

HRID 2289674Notes

Reaction equation

HRID 2289674 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][CH:8]([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].[S:26](=[O:45])(=[O:44])([O:28][C:29]1[C:34]([CH:35]([CH3:37])[CH3:36])=[CH:33][C:32]([N+:38]([O-:40])=[O:39])=[CH:31][C:30]=1[CH:41]([CH3:43])[CH3:42])[NH2:27].C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C)C=O.ClCCl>[CH:35]([C:34]1[CH:33]=[C:32]([N+:38]([O-:40])=[O:39])[CH:31]=[C:30]([CH:41]([CH3:43])[CH3:42])[C:29]=1[O:28][S:26](=[O:45])(=[O:44])[NH:27][C:23](=[O:24])[CH2:22][C:11]1[C:10]([CH:8]([CH3:7])[CH3:9])=[CH:15][C:14]([CH:16]([CH3:18])[CH3:17])=[CH:13][C:12]=1[CH:19]([CH3:21])[CH3:20])([CH3:37])[CH3:36]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 105156412,4,6-Triisopropylphenylacetic acidHCID 186988452,6-Bis(1-methylethyl)-4-nitrophenyl sulfamate

Product 1

HCID 10209327HCID 10209327, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.52 mL, 5.9 mmol) was added dropwise to a solution of 2,4,6-tris(1-methylethyl)-phenyl acetic acid in 150 mL toluene with four drops N,N-dimethylformamide added as a catalyst. The resulting solution was stirred for 4 hours at room temperature and concentrated in vacuo. The residue was redissolved in 200 mL dichloromethane with 2,6-bis(1-methylethyl)-4-nitrophenyl sulfamate (1.50 g, 4.9 mmol) and excess (3 mL) triethylamine and stirred for 16 hours. The reaction was washed with 1 M HCl, dried over MgSO4, filtered, and concentrated to give an oily solid. Recrystallization from hexanes gave 2.37 g (87%) of the title compound as a white solid; mp 85-89° C.

Workup

  1. additionadded as a catalyst
  2. concentrationconcentrated in vacuo
  3. stirringstirred for 16 hours
  4. washThe reaction was washed with 1 M HCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give an oily solid
  9. customRecrystallization from hexanes

Sources & evidence

ORD record
ord-5ced982576ee47c28a5c3f3738bdc64c
Source dataset
uspto-grants-2000_07
Patent number
US06093744

Reaction notes

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