Chloroacetone → HCID 178430862, compound

HRID 1530137Notes

Reaction equation

HRID 1530137 reaction equation
[Br:1][C:2]1[S:3][C:4]([C:15](=[NH:17])[NH2:16])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=2[Cl:14])[N:6]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:25][C:26](=O)[CH3:27]>C(Cl)Cl>[Br:1][C:2]1[S:3][C:4]([C:15]2[NH:16][CH:25]=[C:26]([CH3:27])[N:17]=2)=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=2[Cl:14])[N:6]=1

Participants

5

Reactant 3

HCID 6571Chloroacetone2×HCID 11430Potassium Carbonate2×HCID 580950112-Bromo-4-(2,4-dichlorophenyl)-1,3-thiazole-5-carboximidamide

Product 1

HCID 178430862HCID 178430862, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-bromo-4-(2,4-dichlorophenyl)-1,3-thiazole-5-carboximidamide (70 mg, 0.2 mmol) in DCM (4 mL) was added potassium carbonate (82.7 mg, 0.598 mmol) followed by solution of chloroacetone (50 uL, 0.6 mmol) in DCM (0.4 mL). The mixture was heated to reflux for 3 hours, at which time LCMS indicated ˜50% conversion. Additional chloroacetone (11 ul) and K2CO3 (19 mg) were added and heating was continued for additional 4 hours. LCMS showed complete conversion. Solvent was removed under reduced pressure and the residue was purified using ISCO chromatography, 20%-60% ethyl acetate in hexane to afford the title compound (56 mg, 70%). LCMS: (FA) ES+, 388, 390, 392. 1H NMR (400 MHz, d1-chloroform) δ: 7.60 (dd, J=5.37, 1.71 Hz, 1H), 7.45-7.40 (m, 3H), 2.23 (s, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours, at which time LCMS
  3. temperatureheating
  4. customSolvent was removed under reduced pressure
  5. customthe residue was purified

Sources & evidence

ORD record
ord-593adb3760ad4776b91f7ea920a212e1
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

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