1,2-Dichloroethane → Tert-butyl {2-[(4-formylbenzoyl)amino]phenyl}carbamate

HRID 1919887Notes

Reaction equation

HRID 1919887 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1)=[O:2].[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CCOC(C)=O>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:9])=[CH:10][CH:11]=1)=[O:2]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 120884-Formylbenzoic acidHCID 757711-HydroxybenzotriazoleHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamine

Product 1

HCID 22668143Tert-butyl {2-[(4-formylbenzoyl)amino]phenyl}carbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

4-Formylbenzoic acid (1.50 g, 10.0 mmol), tert-butyl (2-aminophenyl)carbamate (2.08 g, 10.0 mmol), EDC (1.92 g, 10.0 nmol) and HOBt (1.35 g, 10.0 mmol) were dissolved in DMF and the solution was heated at 70° C. for 4 h. The solution was diluted with 200 mL of EtOAc and the organic solution was washed twice with 150 mL of water, then sequentially with 150 mL each of 1 N HCl, NaHCO3 (sat'd), and brine. The solution was dried over MgSO4, concentrated, then purified by flash chromatography (12-100% ethyl acetate in hexanes) to give the desired product, MS cal'd 341 (MH+), exp 341 (MH+).

Workup

  1. washthe organic solution was washed twice with 150 mL of water
  2. dry with materialThe solution was dried over MgSO4
  3. concentrationconcentrated
  4. custompurified by flash chromatography (12-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-a0b94566240b4038b54af921ab9b5678
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

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