Trifluoroacetic acid → HCID 136492456, compound

HRID 508804Notes

Reaction equation

HRID 508804 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]([C:18](=[O:33])[NH:19][C:20](=O)[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[C:23]([O:30][CH3:31])[CH:22]=1)[NH:10]C(OC(C)(C)C)=O.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:18](=[O:33])[NH:19][C:20]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[C:23]([O:30][CH3:31])[CH:22]=2)=[N:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90065653HCID 90065653, compound

Product 1

HCID 136492456HCID 136492456, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(2,6-dichlorophenyl)-2-((3-methoxy-4-nitrobenzoyl)carbamoyl)hydrazinecarboxylate (1.0 g, 2.002 mmol) in DCM (20 mL) was added trifluoro acetic acid (2.0 mL). The reaction mass was stirred at RT for 2-3 h. Excess of solvent was removed at low temperature. The reaction mass was quenched in ice and filter off to afford 0.200 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 3.98 (s, 3H), 7.56-7.62 (m, 2H), 7.69-7.75 (m, 3H), 8.02 (d, J=8.4 Hz, 1H), 11-12 (br s, 1H); MS (m/z): 382.07 (M+H)+.

Workup

  1. customExcess of solvent was removed at low temperature
  2. customThe reaction mass was quenched in ice
  3. filtrationfilter off

Sources & evidence

ORD record
ord-ba6537cb8d88476ca0d6d007cad8ed76
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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