Water → HCID 57812854, compound

HRID 2274408Notes

Reaction equation

HRID 2274408 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]1[CH2:13][O:12][CH2:11][CH2:10][NH:9][CH2:8]1.Cl.[F:15][C:16]1[C:22](F)=[CH:21][C:19]([NH2:20])=[C:18]([N+:24]([O-:26])=[O:25])[CH:17]=1.O>CN(C=O)C>[F:15][C:16]1[C:22]([N:9]2[CH2:8][CH2:7][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:21][C:19]([NH2:20])=[C:18]([N+:24]([O-:26])=[O:25])[CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1571514,5-Difluoro-2-nitroanilineHCID 230902141,4-Oxazepane hydrochloride

Product 1

HCID 57812854HCID 57812854, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

19.4 g of potassium carbonate and 11.9 g of homomorph-oline hydrochloride are added to a solution of 5 g of 4,5-difluoro-2-nitroaniline in 98 mL of anhydrous DMF. The reaction medium is heated at 80° C. using an oil bath for 2 hours. The reaction medium is cooled to ambient temperature, then 300 mL of water are added thereto, and precipitation occurs. The precipitate is filtered through sintered glass. The yellow solid is rinsed with 3 times 100 mL of water. The solid is dried in an oven at 70° C. 6.5 g of 4-fluoro-2-nitro-5-perhydro-1,4-oxazepin-4-ylphenylamine are obtained in the form of an orange solid. 1H NMR (400 MHz, DMSO-d6, δ in ppm): 1.91 (m, 2H); from 3.52 to 3.61 (m, 4H); 3.66 (m, 2H); 3.74 (m, 2H); 6.28 (d, J=8.5 Hz, 1H); 7.24 (broad s, 2H); 7.61 (d, J=15.5 Hz, 1H).

Workup

  1. customfor 2 hours
  2. temperatureThe reaction medium is cooled to ambient temperature
  3. customprecipitation
  4. filtrationThe precipitate is filtered through sintered glass
  5. washThe yellow solid is rinsed with 3 times 100 mL of water
  6. customThe solid is dried in an oven at 70° C

Sources & evidence

ORD record
ord-7e95e20240f9409a8d470706db1fff9d
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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