Dibenzylamine → HCID 10504877, compound

HRID 1975757Notes

Reaction equation

HRID 1975757 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[S:17]([N:20]=[C:21]=[O:22])(=[O:19])=[O:18].[CH:23]([C:26]1[CH:32]=[CH:31][CH:30]=[C:29]([CH:33]([CH3:35])[CH3:34])[C:27]=1[NH2:28])([CH3:25])[CH3:24].C(N(CC)CC)C>O1CCCC1>[CH3:35][CH:33]([C:29]1[CH:30]=[CH:31][CH:32]=[C:26]([CH:23]([CH3:25])[CH3:24])[C:27]=1[NH:28][S:17]([NH:20][C:21](=[O:22])[N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:19])=[O:18])[CH3:34]

Participants

6

Reactant 4

HCID 7656DibenzylamineHCID 8471TriethylamineHCID 32484DiisopropylanilineHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 10504877HCID 10504877, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of dibenzylamine (5.0 g, 25.3 mmol) in 75 mL tetrahydrofuran was added dropwise to a solution of chlorosulfonyl isocyanate (2.21 mL, 25.3 mmol) in 75 mL tetrahydrofuran at 0° C. under an atmosphere of nitrogen. The resulting mixture was warmed to room temperature and stirred for 16 hours. A solution of 2,6-diisopropyl aniline (4.08 g, 23 mmol) and triethylamine (3.5 mL, 25 mmol) in 50 mL tetrahydrofuran was added dropwise and the resulting suspension was stirred for 72 hours. Partitioned between 1N HCl and ethyl acetate. The organic layer was dried with MgSO4, filtered, and evaporated to give an orange oil. Chromatography gave the title compound as a white solid, mp 140°-142° C.

Workup

  1. stirringthe resulting suspension was stirred for 72 hours
  2. customPartitioned between 1N HCl and ethyl acetate
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give an orange oil

Sources & evidence

ORD record
ord-bf438e53dff0495eaa7669d72a9a4a95
Source dataset
uspto-grants-1994_02
Patent number
US05288757

Reaction notes

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