Triethylamine → [(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-(3-dimethylamino-propoxy)-2,6-diisopropyl-phenyl ester

HRID 2289686Notes

Reaction equation

HRID 2289686 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[C:7]([O:13][S:14](=[O:35])(=[O:34])[NH:15][C:16](=[O:33])[CH2:17][C:18]2[C:23]([CH:24]([CH3:26])[CH3:25])=[CH:22][C:21]([CH:27]([CH3:29])[CH3:28])=[CH:20][C:19]=2[CH:30]([CH3:32])[CH3:31])=[C:6]([CH:36]([CH3:38])[CH3:37])[CH:5]=1.C(N(CC)CC)C.Cl.[CH3:47][N:48]([CH3:53])[CH2:49][CH2:50][CH2:51]Cl>CN(C)C=O.O1CCCC1.C(OCC)C>[CH3:47][N:48]([CH3:53])[CH2:49][CH2:50][CH2:51][O:3][C:4]1[CH:5]=[C:6]([CH:36]([CH3:38])[CH3:37])[C:7]([O:13][S:14](=[O:35])(=[O:34])[NH:15][C:16](=[O:33])[CH2:17][C:18]2[C:19]([CH:30]([CH3:32])[CH3:31])=[CH:20][C:21]([CH:27]([CH3:28])[CH3:29])=[CH:22][C:23]=2[CH:24]([CH3:25])[CH3:26])=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 24758Sodium hydrideHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 10142635[(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-hydroxy-2,6-diisopropyl-phenyl ester

Product 1

HCID 10168301[(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-(3-dimethylamino-propoxy)-2,6-diisopropyl-phenyl esterYield 31.4%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Solid sodium hydride (0.16 g, 4 mmol) was added to a solution of [(2,4,6-triisopropyl-phenyl)-acetyl]-sulfamic acid 4-hydroxy-2,6-diisopropyl-phenyl ester (1.0 g, 1.9 mmol) in 50 mL of N,N-dimethylformamide. The resulting mixture was stirred for 1 hour before a mixture of triethylamine (1.08 mL, 7.8 mmol) and 3-dimethylaminopropylchloride hydrochloride (1.22 g, 3.9 mmol) in 75 mL tetrahydrofuran was added dropwise. The resulting mixture was stirred for 16 hours and then concentrated in vacuo. The residue was partitioned between saturated citric acid and dichloromethane. The organic layer was dried over magnesium sulfate, filtered, and concentrated to give an oily solid. Trituration with a small amount of diethyl ether gave 0.36 g of [(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-(3-dimethylamino-propoxy)-2,6-diisopropyl-phenyl ester as a white foam.

Workup

  1. additionwas added dropwise
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between saturated citric acid and dichloromethane
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oily solid

Sources & evidence

ORD record
ord-ed8a7975289e44e49e187b0fb7b5a82c
Source dataset
uspto-grants-2000_07
Patent number
US06093744

Reaction notes

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