2-Chloro-5-methylaniline → HCID 21093758, compound

HRID 1350042Notes

Reaction equation

HRID 1350042 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:3]=1[NH2:4].[O-:10][C:11]#[N:12].[K+]>C(O)(=O)C.O>[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:3]=1[NH:4][C:11]([NH2:12])=[O:10]

Participants

5

Reactant 2

HCID 667702-Chloro-5-methylanilineHCID 11378442Potassium cyanate

Product 1

HCID 21093758HCID 21093758, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 2-chloro-5-methylaniline (10 g, 70.6 mmol) and potassium cyanate (14.3 g, 176 mmol) in a mixture of acetic acid (340 mL) and water (34 mL) was stirred at room temperature during 4 hours. The solvent was evaporated and the residue taken into a mixture of CH2Cl2 and an aqueous saturated solution of NaHCO3. The precipitate was filtered, washed with dichloromethane and dried under vacuum to give 12.6 g (97%) of intermediate 7.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue taken into a mixture of CH2Cl2
  3. filtrationThe precipitate was filtered
  4. washwashed with dichloromethane
  5. customdried under vacuum

Sources & evidence

ORD record
ord-decb852d89a34f7c8c66f9067f181bb3
Source dataset
uspto-grants-2007_05
Patent number
US07214676B2

Reaction notes

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