Hexane → HCID 70107072, compound

HRID 2184903Notes

Reaction equation

HRID 2184903 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Al](C)C.[CH3:26]CCCCC.[C:32]([C:34]1[CH:35]=[C:36](/[CH:40]=[CH:41]\[C:42]([O:44]CC)=O)[CH:37]=[CH:38][CH:39]=1)#[N:33]>ClCCl>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:42](=[O:44])/[CH:41]=[C:40](\[C:36]2[CH:37]=[CH:38][CH:39]=[C:34]([C:32]#[N:33])[CH:35]=2)/[CH3:26])=[CH:17][CH:16]=1)(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8058HexaneHCID 10804475N-tert-butyl-4'-aminobiphenyl-2-sulfonamideHCID 16682925TrimethylaluminumHCID 86758107HCID 86758107, compound

Product 1

HCID 70107072HCID 70107072, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2′-tert-butylaminosulfonyl-4-amino-[1,1′]-biphenyl (198 mg, 0.65 mmol) in 5 ml anhydrous dichloromethane was added a solution of 2M trimethylaluminum in hexane (0.98 ml, 1.95 mmol). Reaction was stirred at room temperature for 20 minutes to which a solution of ethyl (Z) 3-(3-cyanophenyl)-2-propenoate (140 mg, 0.65 mmol) in 1 ml anhydrous dichloromethane was added. Reaction was stirred at room temperature overnight. Reaction was quenched with 5 ml 1N HCl after which an additional 20 ml dichloromethane was added. Organic was washed with 2×25 ml water, dried over magnesium sulfate and concentrated to give (2Z)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)but-2-enamide (200 mg, 65%) as a light brown residue which was sufficiently pure to be used without further purification.

Workup

  1. customReaction
  2. additionwas added
  3. customReaction
  4. customReaction
  5. customwas quenched with 5 ml 1N HCl after which an additional 20 ml dichloromethane
  6. additionwas added
  7. washOrganic was washed with 2×25 ml water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-84540a1a21b04b23835ebb1ee0e219d0
Source dataset
uspto-grants-2002_06
Patent number
US06399627B1

Reaction notes

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