Sodium Iodide → HCID 67313226, compound

HRID 222062

Reaction equation

HRID 222062 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[OH:11].Cl.Cl[CH2:14][C:15]1[N:16]=[CH:17][S:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C.C(Cl)Cl.O>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[O:11][CH2:14][C:15]1[N:16]=[CH:17][S:18][CH:19]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 12074NitrofunginHCID 27632894-(Chloromethyl)-1,3-thiazole hydrochloride

Product 1

HCID 67313226HCID 67313226, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloro-4-nitrophenol (1.00 g, 5.76 mmol) in acetonitrile (125 mL) were added 4-chloromethylthiazole hydrochloride (1.08 g, 6.34 mmol), Potassium carbonate (2.39 g, 17.29 mmol) and sodium iodide (1.73 g, 11.52 mmol). The reaction mixture was stirred at 60 C overnight. Water (60 mL) and DCM (10 mL) were added. After all solid material dissolved, layers formed were separated. The organic layer was washed with water and brine, dried over Na2SO4 and concentrated down to give the required material as a light yellow solid (1.29 mg, 83%). 1H-NMR (CD2Cl2) δ 8.87 (d, 1H), 8.32 (d, 1H), 8.16 (dd, 1H), 7.54-7.56 (m, 1H), 7.22 (d, 1H), 5.33-5.34 (m, 2H); LCMS RT=3.01 min; [M+H]+=271.0.

Workup

  1. dissolutionAfter all solid material dissolved
  2. customlayers formed
  3. customwere separated
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated down

Sources & evidence

ORD record
ord-407926c603784d78906a5cde6a1da983
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Linked notes

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