1,2-Dichloroethane → HCID 58433956, compound

HRID 2363243Notes

Reaction equation

HRID 2363243 reaction equation
[C:1]([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25].CN(C=O)C.C(Cl)CCl>O>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:11])=[CH:12][CH:13]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 19266p-Acetamidobenzoic acidHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamine

Product 1

HCID 58433956HCID 58433956, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 1 L round-bottom flask, were added 4-acetamidobenzoic acid (21.7 g, 122 mmol), tert-butyl (2-aminophenyl)carbamate (23.0 g, 111 mmol), and DMF (90 mL). The mixture was stirred to dissolve under N2, before EDC (27.6 g, 144 mmol) was added in one portion. The reaction mixture was stirred for 2 h, and water (270 mL) was added and stirred for 2 h. The precipitates were filtered, washed with water (2×45 mL) and heptane (2×45 mL). The filter cake was dried at 40° C. in vacuo for 16 h to afford tert-butyl (2-(4-acetamidobenzamido) phenyl)carbamate (31.8 g, 78% yield, 90.6% HPLC purity) as a white solid.

Workup

  1. additionwas added in one portion
  2. stirringThe reaction mixture was stirred for 2 h
  3. stirringstirred for 2 h
  4. filtrationThe precipitates were filtered
  5. washwashed with water (2×45 mL) and heptane (2×45 mL)
  6. customThe filter cake was dried at 40° C. in vacuo for 16 h

Sources & evidence

ORD record
ord-b9992b077a474ae1afaeb231ec96c901
Source dataset
uspto-grants-2014_04
Patent number
US08691875B2

Reaction notes

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