Water → HCID 59593262, compound

HRID 1024214Notes

Reaction equation

HRID 1024214 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.Cl[C:20]1[S:21][C:22]([CH:26]=[O:27])=[C:23]([Cl:25])[N:24]=1.O>O1CCCC1>[Cl:25][C:23]1[N:24]=[C:20]([NH:7][CH2:6][C:5]2[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=2)[S:21][C:22]=1[CH:26]=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 660364-ChlorobenzylamineHCID 81531DiisopropylethylamineHCID 14886722,4-Dichloro-1,3-thiazole-5-carboxaldehyde

Product 1

HCID 59593262HCID 59593262, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of p-chlorobenzylamine (61, 283 mg, 2.00 mmol) and N,N-Diisopropylethylamine (0.697 mL) in tetrahydrofuran (20 mL) was slowly added 2,4-Dichloro-thiazole-5-carbaldehyde (93, 364 mg, 2.00 mmol) in tetrahydrofuran (10 mL) at room temperature. The reaction was stirred at room temperature overnight. The reaction mixture was poured into iced water, extracted with ethyl acetate, washed with brine, and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexane to provide the compound as a yellow solid (94, 0.3 g, 50%). MS (ESI) [M−H+]=286.97.

Workup

  1. customat room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customAfter removal of solvent
  6. customthe residue was purified by silica gel column chromatography
  7. washeluting with ethyl acetate in hexane

Sources & evidence

ORD record
ord-3ed5391d4b9541ccb0f9fb1812d975fa
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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