Dichloromethane → HCID 22380011, compound

HRID 1988773Notes

Reaction equation

HRID 1988773 reaction equation
Cl[CH2:2][C:3]1[N:4]([CH2:15][CH3:16])[C:5]2[CH:11]=[C:10]([C:12](=[O:14])[CH3:13])[CH:9]=[CH:8][C:6]=2[N:7]=1.[NH:17]1[CH:21]=[CH:20][N:19]=[C:18]1[C:22]1[S:23][CH:24]=[CH:25][N:26]=1.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>CN(C=O)C.[Cl-].[Na+].O>[CH2:15]([N:4]1[C:5]2[CH:11]=[C:10]([C:12](=[O:14])[CH3:13])[CH:9]=[CH:8][C:6]=2[N:7]=[C:3]1[CH2:2][N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[C:22]1[S:23][CH:24]=[CH:25][N:26]=1)[CH3:16]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 222603952-(1H-Imidazol-2-yl)-1,3-thiazoleHCID 223801501-(2-Chloromethyl-3-ethyl-3H-benzoimidazol-5-yl)-ethanone

Product 1

HCID 22380011HCID 22380011, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 1-(2-Chloromethyl-3-ethyl-3H-benzoimidazol-5-yl)-ethanone (150 mg, 0.63 mmol), 2-(1H-Imidazol-2-yl)-thiazole (95 mg, 0.63 mmol) and K2CO3 (262 mg, 1.9 mmol) in DMF (10 mL) is stirred at room temperature for 48 hours. Brine (6 mL) and DCM (20 mL) are added. The organic layer is separated and the aqueous layer is extracted with DCM (3×29 mL). The combined organic layers are dried and solvent removed. The residue is purified by PTLC (10% methanol in DCM) to give 1-[3-Ethyl-2-(2-thiazol-2-yl-imidazol-1-ylmethyl)-3H-benzoimidazol-5-yl]-ethanone as a solid. 1H NMR (CDCl3) δ 8.05 (d, 1H), 7.92 (dd, 1H), 7.87 (dd, 1H), 7.81 (dd, 1H), 7.40 (d, 1H), 7.20 (d, 1H), 7.14 (d, 1H), 6.17 (s, 2H), 4.3.3 (q, 2H), 2.67 (s, 3H), 1.13 (t, 3H).

Workup

  1. customThe organic layer is separated
  2. extractionthe aqueous layer is extracted with DCM (3×29 mL)
  3. customThe combined organic layers are dried
  4. customsolvent removed
  5. customThe residue is purified by PTLC (10% methanol in DCM)

Sources & evidence

ORD record
ord-9469def574d84379842f73b3499200ad
Source dataset
uspto-grants-2010_01
Patent number
US07642267B2

Reaction notes

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