Sodium Hydroxide → HCID 66937074, compound

HRID 408739Notes

Reaction equation

HRID 408739 reaction equation
[Cl:1][C:2]1[C:11]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:10][C:5]2[NH:6][C:7](=O)[NH:8][C:4]=2[CH:3]=1.O=P(Cl)(Cl)[Cl:19].[OH-].[Na+]>>[Cl:19][C:7]1[NH:8][C:4]2[CH:3]=[C:2]([Cl:1])[C:11]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:10][C:5]=2[N:6]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 66937164HCID 66937164, compound

Product 1

HCID 66937074HCID 66937074, compoundYield 96%

Procedure

Thoroughly dried 5-chloro-6-trifluoromethoxy-1,3-dihydro-benzoimidazol-2-one (154.6 g, 0.61 mol, 1.0 equiv.) was suspended in POCl3 (450 mL, 8.0 equiv.). The reaction solution was heated to reflux temperature for 6 hours and cooled to room temperature. The solution was poured into crushed ice/water (˜3 L) slowly with sufficient stirring. The solution was neutralized to pH=6.0 with NaOH. The precipitated solid was collected by filtration, washed with water, and dried to afford the title compound (159.97 g, 96%). The crude product was used in the following reaction without further purification.

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureto reflux temperature for 6 hours
  3. additionThe solution was poured
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-4341567161f44f7ebcc2c7f1a768449f
Source dataset
uspto-grants-2014_06
Patent number
US08759345B2

Reaction notes

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