Benzhydrylamine → HCID 10624052, compound

HRID 1975754Notes

Reaction equation

HRID 1975754 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-4e95a1bd522d46ec9bff5493bcd69ae2
Source dataset
uspto-grants-1994_02
Patent number
US05288757

Reaction notes

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