Triethylamine → HCID 18621653, compound

HRID 1861863Notes

Reaction equation

HRID 1861863 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:5]([O:7][CH3:8])=[O:6].C(N(CC)CC)C.Cl[C:28](Cl)([O:30]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[C:16]([O:15][C:13]([N:12]1[C:11]2[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=2[NH:1][C:28]1=[O:30])=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 18621647Methyl 3-amino-4-[(tert-butoxycarbonyl)amino]benzoate

Product 1

HCID 18621653HCID 18621653, compoundYield 171.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Part 2. To a chilled solution of methyl 3-amino-4-[(tert-butoxy)carbonylamino]benzoate (0.40 g, 1.5 mmol) in CH2Cl2 (10 mL) and triethylamine (0.21 mL, 1.5 mmol) was added a solution of triphosgene (161 mg, 0.54 mmol) in CH2Cl2 (6 mL) over 5 min. The reaction was stirred at room temperature for 2 hr, diluted with CH2Cl2, washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by silica gel chromatography using 50% ethyl acetate in CH2Cl2 as eluent to give methyl 1-[(tert-butyl)oxycarbonyl]-2-oxo-(3H)—benzimidazole-5-carboxylate (0.27 g, 61%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f86fad79ae49423a97fec73524db8923
Source dataset
uspto-grants-2003_03
Patent number
US06534535B1

Reaction notes

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