Pyridine → HCID 67254175, compound

HRID 1821749Notes

Reaction equation

HRID 1821749 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([NH2:12])=[CH:6][C:5]=1[C:13]([F:16])([F:15])[F:14].N1C=CC=CC=1.Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=1)=[O:26]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([NH:12][C:25]([O:27][C:28]2[CH:29]=[CH:30][C:31]([N+:34]([O-:36])=[O:35])=[CH:32][CH:33]=2)=[O:26])=[CH:6][C:5]=1[C:13]([F:14])([F:16])[F:15]

Participants

5

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 67254453HCID 67254453, compound

Product 1

HCID 67254175HCID 67254175, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 5-methoxy-4-amino-2-trifluoromethyl-benzoic acid methyl ester (552 mg, 2.22 mmol) in 6.6 mL CH2Cl2 at 0° C. under nitrogen was added pyridine (180 μL, 2.22 mmol) followed p-nitrophenyl chloroformate (448 mg, 2.22 mmol) as a solid. After stirring for 1 hour, the reaction was diluted to 30 mL with CH2Cl2 and washed 2×30 mL with 2N HCl and 1×30 mL with H2O. The organics were dried (MgSO4), filtered and concentrated to the p-nitrophenyl carbamate which was isolated as a white foam (878 mg, 96%). 1H-NMR (400 MHz, CDCl3) δ 8.57 (br s, 1H), 8.30 (d, 2H), 7.77 (br s, 1H), 7.40 (d, 2H), 7.37 (s, 1H), 4.03 (s, 3H), 3.94 (s, 3H).

Workup

  1. washwashed 2×30 mL with 2N HCl and 1×30 mL with H2O
  2. dry with materialThe organics were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated to the p-nitrophenyl carbamate which

Sources & evidence

ORD record
ord-d82ff1ec682740e885df6827dd51dd77
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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