Hydrochloric Acid → HCID 59208447, compound

HRID 655748Notes

Reaction equation

HRID 655748 reaction equation
N[C:2]1[S:3][C:4]([C:16]([O:18][CH3:19])=[O:17])=[C:5]([C:7]2[N:8]([CH2:12][CH2:13][O:14][CH3:15])[CH:9]=[CH:10][N:11]=2)[N:6]=1.[ClH:20].N([O-])=O.[Na+].NC(N)=O>C(O)(=O)C.O>[Cl:20][C:2]1[S:3][C:4]([C:16]([O:18][CH3:19])=[O:17])=[C:5]([C:7]2[N:8]([CH2:12][CH2:13][O:14][CH3:15])[CH:9]=[CH:10][N:11]=2)[N:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 23668193Sodium NitriteHCID 59208395HCID 59208395, compound2×

Product 1

HCID 59208447HCID 59208447, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

Methyl 2-amino-4-[1-(2-methoxyethyl)-1H-imidazol-2-yl]-1,3-thiazole-5-carboxylate (Intermediate 5; 0.55 g, 2.2 mmol) was suspended in glacial acetic acid (20 ml) and concentrated HCl (30 ml). The solution was cooled to 0° C. and to this a solution of sodium nitrite in water (15 ml) was added dropwise. After stirring at 0° C. for 10 mins, the reaction was slowly warmed to room temperature and stirred for 1 hour. Once complete by LCMS, a solution of urea (0.25 g) in water (10 ml) was added dropwise. After stirring at room temperature for 30 mins, solvent was removed under reduced pressure. The residue was partitioned with sat. NaHCO3 (aq) and EtOAc. Extraction with EtOAc (×3), drying with MgSO4 and concentrating yielded an orange oil which was used without purification (0.20 g). MS (ES) (M+H)+: 302 for C11H12ClN3O3S; NMR: 3.34 (s, 3H), 3.62 (m, 2H), 3.81 (s, 3H), 4.22 (m, 2H), 7.24 (s, 2H).

Workup

  1. temperaturethe reaction was slowly warmed to room temperature
  2. stirringstirred for 1 hour
  3. stirringAfter stirring at room temperature for 30 mins
  4. customsolvent was removed under reduced pressure
  5. customThe residue was partitioned with sat. NaHCO3 (aq) and EtOAc
  6. extractionExtraction with EtOAc (×3)
  7. dry with materialdrying with MgSO4
  8. concentrationconcentrating
  9. customyielded an orange oil which
  10. customwas used without purification (0.20 g)

Sources & evidence

ORD record
ord-09ab2f6aab8841428750179ab7b60a73
Source dataset
uspto-grants-2011_12
Patent number
US08071605B2

Reaction notes

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