Water → HCID 22668128, compound

HRID 658030Notes

Reaction equation

HRID 658030 reaction equation
[Cl-].[CH3:2][O:3][C:4](=[O:14])[C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1.[C:15]([O:19][C:20](=[O:29])[NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH2:28])([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C.O>ClCCl>[C:15]([O:19][C:20]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:28][C:9](=[O:11])[C:8]1[CH:7]=[CH:6][C:5]([C:4]([O:3][CH3:2])=[O:14])=[CH:13][CH:12]=1)=[O:29])([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 53442854Terephthalic acid monomethylester chloride

Product 1

HCID 22668128HCID 22668128, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under ice cooling, terephthalic acid monomethylester chloride (1.1 g, 5.0 mmol) was added to a solution of 2-aminophenylcarbamic acid t-butyl ester (Reference Compound No. 1-1, 1.1 g, 5.0 mmol) and triethylamine (30 mL) in dichloromethane (15 mL), and then the mixture was stirred at room temperature for 4 hours. Water (50 mL) was added thereto, and the whole was extracted with ethyl acetate (40 mL) twice. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The resulting solid was collected by filtration with a mixed solvent (hexane (10 mL) and ethyl acetate (5 mL)), and the whole was dried under reduced pressure to give 1.8 g of the title reference compound as a white solid. (Yield 99%)

Workup

  1. extractionthe whole was extracted with ethyl acetate (40 mL) twice
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. filtrationThe resulting solid was collected by filtration with a mixed solvent (hexane (10 mL) and ethyl acetate (5 mL))
  5. customthe whole was dried under reduced pressure
  6. customto give 1.8 g of the title reference compound as a white solid

Sources & evidence

ORD record
ord-c3c7ddc4e1574f3e95498a6ce2056b43
Source dataset
uspto-grants-2011_12
Patent number
US08076332B2

Reaction notes

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