Dibenzylamine → HCID 10504877, compound

HRID 249562Notes

Reaction equation

HRID 249562 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-aa8aa806394b466686127a4bd6868771
Source dataset
uspto-grants-1993_05
Patent number
US05214206

Reaction notes

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