Benzhydrylamine → HCID 10624052, compound

HRID 249559Notes

Reaction equation

HRID 249559 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14]([NH:16][S:17](Cl)(=[O:19])=[O:18])=[O:15])[CH3:3].[CH:21]([NH2:34])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>CCOCC>[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14]([NH:16][S:17]([NH:34][CH:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:19])=[O:18])=[O:15])[CH3:3]

Participants

5

Reactant 3

HCID 7036BenzhydrylamineHCID 8471TriethylamineHCID 10615554HCID 10615554, compound

Product 1

HCID 10624052HCID 10624052, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of [[[2,6-bis(1-methylethyl)phenyl]amino]carbonyl]sulfamoyl chloride (1.0 g, 3.1 mmoles) in 60 mL Et2O was added dropwise to a solution of benzhydrylamine (0.56 g, 3.1 mmoles) and 0.5 mL triethylamine (3.4 mmoles) in 60 mL Et2O at -15° C. (acetone/ice bath) under an atmosphere of N2. The resulting suspension was warmed to 25° C. and stirred for 16 hours. This was then partitioned between 1N HCl and EtOAc. The EtOAc layer was dried with MgSO4, filtered, and evaporated to give an off white solid. Chromatography (SiO2, 30% EtOAc/hexanes) gave 0.49 g (34%) of the title compound as a white solid, mp 182°-185° C.

Workup

  1. customThis was then partitioned between 1N HCl and EtOAc
  2. dry with materialThe EtOAc layer was dried with MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customto give an off white solid

Sources & evidence

ORD record
ord-7044940928cb443595c32e4222c50b55
Source dataset
uspto-grants-1993_05
Patent number
US05214206

Reaction notes

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