Ammonia → HCID 66682859, compound

HRID 530303Notes

Reaction equation

HRID 530303 reaction equation
S(Cl)(Cl)=[O:2].[CH3:5][C:6]1([CH3:25])[CH2:10][O:9][CH2:8][N:7]1[C:11]([N:13]1[C:17]2[CH:18]=[C:19](C(O)=O)[CH:20]=[CH:21][C:16]=2[N:15]=[N:14]1)=[O:12].[N:26]1[CH:31]=CC=CC=1.N>ClCCl.C(O)C.O>[CH3:25][C:6]1([CH3:5])[CH2:10][O:9][CH2:8][N:7]1[C:11]([N:13]1[C:17]2[CH:18]=[CH:19][C:20]([C:31]([NH2:26])=[O:2])=[CH:21][C:16]=2[N:15]=[N:14]1)=[O:12]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 66688155HCID 66688155, compound

Product 1

HCID 66682859HCID 66682859, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.633 mL, 8.67 mmol) was added dropwise to a stirred solution of 1-(4,4-dimethyloxazolidine-3-carbonyl)-1H-benzo[d][1,2,3]triazole-6-carboxylic acid (0.763 g, 2.63 mmol) and pyridine (0.702 mL, 8.67 mmol) in dichloromethane (17 mL) at room temperature. The yellow solution was allowed to stir at room temperature for 15 minutes. This solution was then added dropwise to a 1.75 N solution of ammonia (15.02 mL, 26.3 mmol) in ethanol at 0° C., whereupon a white suspension formed. The reaction mixture was allowed to stir at room temperature for a further 30 minutes. Water was added and the ethanol was evaporated. Then the residue was diluted with dichloromethane, and the organic layer was separated and washed with 1 N HCl solution. The organic layer was dried (MgSO4), filtered and evaporated to give a yellow solid. The solid was recrystallised from a dichloromethane/ethanol mixture to give the product as a beige solid (151 mg, 20%).

Workup

  1. customformed
  2. stirringto stir at room temperature for a further 30 minutes
  3. customthe ethanol was evaporated
  4. additionThen the residue was diluted with dichloromethane
  5. customthe organic layer was separated
  6. washwashed with 1 N HCl solution
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customto give a yellow solid
  11. customThe solid was recrystallised from a dichloromethane/ethanol mixture

Sources & evidence

ORD record
ord-d47abe22bb2f4137a56bb178ec9c639d
Source dataset
uspto-grants-2016_05
Patent number
US09353082B2

Reaction notes

Loading…