Hydrochloric Acid → HCID 86660263, compound

HRID 245339Notes

Reaction equation

HRID 245339 reaction equation
Br[C:2]1([C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([O:10][CH:11]([F:13])[F:12])[CH2:4]1)[NH2:3].[Cu][C:15]#[N:16].C(N)CN.Cl>CN(C=O)C.O>[C:15]([C:2]1([C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([O:10][CH:11]([F:13])[F:12])[CH2:4]1)[NH2:3])#[N:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3301EthylenediamineHCID 86660261HCID 86660261, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 86660263HCID 86660263, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
150 °C

Procedure

1-Bromo-3-difluoromethoxy-6-methylaniline (1.70 g, 6.74 mmol) is initially charged in 7 ml of DMF, and copper(I) cyanide (0.79 g, 8.76 mmol) is added. The reaction is stirred at 150° C. overnight. After cooling to room temperature, the DMF is removed under reduced pressure and 15 ml of water and ethylenediamine (3.6 ml, 53.9 mmol) are added to the residue. The mixture is then stirred at room temperature for 1 hour. The reaction mixture is then acidified to pH=5 using hydrochloric acid, and the aqueous phase is extracted with ethyl acetate (6 times). The combined organic phases are dried over sodium sulphate and then purified chromatographically on silica gel. (logP: 1.90; MH+: 199, 1H-NMR (400 MHz, DMSO, ppm): 2.12 (s, 3H), 5.91, (s, 2H), 7.10 (t, 1H), 7.20 (m, 2H).

Workup

  1. temperatureAfter cooling to room temperature
  2. additionare added to the residue
  3. stirringThe mixture is then stirred at room temperature for 1 hour
  4. extractionthe aqueous phase is extracted with ethyl acetate (6 times)
  5. dry with materialThe combined organic phases are dried over sodium sulphate
  6. custompurified chromatographically on silica gel

Sources & evidence

ORD record
ord-b00b4b9a3e3e4c8a972771f0774707ec
Source dataset
uspto-grants-2014_02
Patent number
US08658800B2

Reaction notes

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