Triethylamine → HCID 58958458, compound

HRID 915169Notes

Reaction equation

HRID 915169 reaction equation
[CH3:1][N:2](/[CH:4]=[N:5]/[C:6]1[S:7][C:8]([C:11]([OH:13])=O)=[CH:9][N:10]=1)[CH3:3].S(Cl)(Cl)=O.C(N(CC)CC)C.[CH:25]1([NH2:28])[CH2:27][CH2:26]1>>[CH:25]1([NH:28][C:11]([C:8]2[S:7][C:6](/[N:5]=[CH:4]/[N:2]([CH3:1])[CH3:3])=[N:10][CH:9]=2)=[O:13])[CH2:27][CH2:26]1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 69828CyclopropylamineHCID 58958434HCID 58958434, compound

Product 1

HCID 58958458HCID 58958458, compound

Conditions

Temperature
25 °C

Procedure

To a 100 mL flask was charged 2-{[(1E)-(dimethylamino) methylidene]amino}-1,3-thiazole-5-carboxylic acid 23-2 (0.56 g, 2.37 mmol) and thionyl chloride (5 mL). This suspension was refluxed for 75 minutes. At the end of this time the homogeneous solution was evaporated to dryness and the residue was flushed 2 times with CCl4. This residue was then dissolved in methylene chloride and triethylamine (1.20 g, 11.8 mmol) was added followed by cyclopropylamine (0.47 g, 8.29 mmol). The reaction was stirred overnight at 25° C. A precipitate was filtered off. Hi-Res MS: calc: 239.0961 found: 239.0959. 1H-NMR (DMSO): 8.36 ppm (s, 1H); 8.27 ppm (s, 1H); 7.83 ppm (s, 1H); 3.12 ppm (s, 3H); 2.98 ppm (s, 3H); 2.72 ppm (m, 1H); 0.67 ppm (m, 2H); 0.52 ppm (m, 2H).

Workup

  1. temperatureThis suspension was refluxed for 75 minutes
  2. customAt the end of this time the homogeneous solution was evaporated to dryness
  3. customthe residue was flushed 2 times with CCl4
  4. dissolutionThis residue was then dissolved in methylene chloride
  5. filtrationA precipitate was filtered off

Sources & evidence

ORD record
ord-4cc1fb6a37dd4c919a92fb11da62d0fa
Source dataset
uspto-grants-2007_09
Patent number
US07265134B2

Reaction notes

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