3-tert-Butylaniline → HCID 11662008, compound

HRID 555400Notes

Reaction equation

HRID 555400 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH2:8])([CH3:4])([CH3:3])[CH3:2].[C:12]([C:16]1[CH:31]=[CH:30][CH:29]=[CH:28][C:17]=1[O:18][C:19]1[C:24]([N:25]=[C:26]=[S:27])=[CH:23][CH:22]=[CH:21][N:20]=1)([CH3:15])([CH3:14])[CH3:13]>ClCCCl>[C:12]([C:16]1[CH:31]=[CH:30][CH:29]=[CH:28][C:17]=1[O:18][C:19]1[C:24]([NH:25][C:26]([NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=2)=[S:27])=[CH:23][CH:22]=[CH:21][N:20]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 793343-tert-ButylanilineHCID 59857388HCID 59857388, compound

Product 1

HCID 11662008HCID 11662008, compoundYield 104.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 3-tert-butylaniline (104 mg, 0.70 mmol) in DCE (3 mL) was slowly added 1c (100 mg, 0.35 mmol). The reaction was stirred 18 h at rt and concentrated. The crude mixture was dissolved in methanol and filtered through an SCX cartridge and concentrated to afford 97a (158 mg, quantitative) as a yellow oil. This material was carried to the next step without further purification.

Workup

  1. concentrationconcentrated
  2. dissolutionThe crude mixture was dissolved in methanol
  3. filtrationfiltered through an SCX cartridge
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2cc5ece6320a4d4a9b9f4e6ca5a2922a
Source dataset
uspto-grants-2011_11
Patent number
US08053450B2

Reaction notes

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