3-Methoxy-4-nitrobenzoyl isocyanate → HCID 90065653, compound

HRID 508803Notes

Reaction equation

HRID 508803 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:28]=[CH:29][C:30]=1[N+:31]([O-:33])=[O:32])[C:23]([N:25]=[C:26]=[O:27])=[O:24]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]([C:26](=[O:27])[NH:25][C:23](=[O:24])[C:22]1[CH:28]=[CH:29][C:30]([N+:31]([O-:33])=[O:32])=[C:20]([O:19][CH3:18])[CH:21]=1)[NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 900189023-Methoxy-4-nitrobenzoyl isocyanateHCID 90065648Tert-butyl 2-(2,6-dichlorophenyl)hydrazinecarboxylate

Product 1

HCID 90065653HCID 90065653, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(2,6-dichlorophenyl)hydrazinecarboxylate (Intermediate-44, 1.2 g, 4.5 mmol) in DCM (20 mL) was added 3-methoxy-4-nitrobenzoyl isocyanate (1.0 g, 4.5 mmol). The reaction mass was stirred at RT for 2 h. Excess of solvent was removed under vacuum to afford 1.5 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 1.35 (s, 9H), 3.97 (s, 3H), 7.89 (m, 1H), 7.27-7.35 (m, 2H), 7.55 (d, 1H), 7.62-7.75 (m, 1H), 7.94 (d, 1H), 8.26 (s, 1H), 9.03 (s, 1H); MS (m/z): 496.78 (M−H)−.

Workup

  1. customExcess of solvent was removed under vacuum

Sources & evidence

ORD record
ord-7acb311010a74c8d9e7712a99b1922e6
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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