Potassium cyanate → HCID 79777002, compound

HRID 929176Notes

Reaction equation

HRID 929176 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([NH:6][CH2:7][C:8]([O:10]CC)=O)=[CH:4][C:3]=1[F:15].[O-:16][C:17]#[N:18].[K+]>C(O)(=O)C.O>[Br:1][C:2]1[CH:14]=[CH:13][C:5]([N:6]2[CH2:7][C:8](=[O:10])[NH:18][C:17]2=[O:16])=[CH:4][C:3]=1[F:15]

Participants

5

Reactant 2

HCID 11378442Potassium cyanateHCID 65435733HCID 65435733, compound

Product 1

HCID 79777002HCID 79777002, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a solution of ethyl 2-(4-bromo-3-fluoro-anilino)acetate (86 g, 0.31 mol) in acetic acid (1.5 L) and water (100 mL) was added a solution of potassium cyanate (50 g, 0.6 mol) in water (200 mL). The reaction mixture was stirred at room temperature for 12 h and then evaporated to dryness. Then 1.5 L of 25% HCl was added to the residue and the mixture was heated to reflux for 3 h. After cooling to room temperature, the solid was filtered and dried to give the title compound. LC-MS: calculated for C9H6BrFN2O2 271.96 observed m/e: 273.35 (M+H)+ (Rt 3.44/6.5 min).

Workup

  1. customevaporated to dryness
  2. additionThen 1.5 L of 25% HCl was added to the residue
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 3 h
  5. temperatureAfter cooling to room temperature
  6. filtrationthe solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-7bd6cd4370044d67b7ffdf0fef1ceb35
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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