Sodium Bicarbonate → HCID 24959791, compound

HRID 1873605Notes

Reaction equation

HRID 1873605 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]([C:16]#[N:17])=[C:4]([SH:18])[N:3]=1.Cl[CH2:20][C:21]1[N:22]=[C:23]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[S:24][CH:25]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C.O>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]([C:16]#[N:17])=[C:4]([S:18][CH2:20][C:21]2[N:22]=[C:23]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[S:24][CH:25]=2)[N:3]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazoleHCID 178510475HCID 178510475, compound

Product 1

HCID 24959791HCID 24959791, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2.00 g (5.42 mmol) of the compound from Example 33A are initially charged in 111 ml of dry DMF, and 1.46 g (5.96 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole and 1.82 g (21.68 mmol) of sodium bicarbonate are added. The reaction mixture is stirred at RT for 12 h. The mixture is then diluted with 20 ml of water and extracted twice with in each case 100 ml of ethyl acetate. The combined organic phases are washed once with 15 ml of saturated aqueous sodium bicarbonate solution and dried over magnesium sulfate. After removal of the solvent the residue is purified chromatographically on silica gel 60 (mobile phase: gradient cyclohexane/ethyl acetate 50:1→2:1).

Workup

  1. extractionextracted twice with in each case 100 ml of ethyl acetate
  2. washThe combined organic phases are washed once with 15 ml of saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customAfter removal of the solvent the residue
  5. customis purified chromatographically on silica gel 60 (mobile phase: gradient cyclohexane/ethyl acetate 50:1→2:1)

Sources & evidence

ORD record
ord-4cf316378f734158890a71c9c08c8726
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

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