Hydrochloric Acid → HCID 20145095, compound

HRID 1906011Notes

Reaction equation

HRID 1906011 reaction equation
FC(F)(F)C(O)=O.[CH3:8][NH:9][C:10]1[S:11][C:12]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[C:13]([C:15](=O)[NH2:16])[N:14]=1.Cl.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.N1C=CC=CC=1>[C:15]([C:13]1[N:14]=[C:10]([NH:9][CH3:8])[S:11][C:12]=1[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)#[N:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 20144953HCID 20144953, compound

Product 1

HCID 20145095HCID 20145095, compoundYield 25.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2.8 g) was dropwise added to a suspension of 2-methylamino-4-carbamoyl-5-(4-pyridyl)thiazole (2.1 g) and pyridine (2.8 g) in methylene chloride (60 ml) at 5° to 10° C. with stirring, which was continued under the same condition for 6 hours. The reaction mixture was poured into ice-water and the resultant mixture was acidified to pH 1.0 with 10% hydrochloric acid. The separated aqueous layer was adjusted to pH 7.5 with 20% potassium carbonate and extracted with ethyl acetate. The organic extract was washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo to give a crystalline residue, which was recrystallized from a mixture of ethyl acetate and tetrahydrofuran to afford 4-cyano-2-methylamino-5-(4-pyridyl)thiazole (0.5 g). mp 192°-195° C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customto give a crystalline residue, which
  7. customwas recrystallized from a mixture of ethyl acetate and tetrahydrofuran

Sources & evidence

ORD record
ord-819ec82e6d8246f3a2327ffa764c4359
Source dataset
uspto-grants-1987_03
Patent number
US04649146

Reaction notes

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