1,2-Dichloroethane → HCID 58433956, compound

HRID 1776957Notes

Reaction equation

HRID 1776957 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 tier 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 tier 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-780952572c0648bdb320678c4b50172f
Source dataset
uspto-grants-2016_02
Patent number
US09266822B2

Reaction notes

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