1,2-Dichloroethane → HCID 86610489, compound

HRID 2416186Notes

Reaction equation

HRID 2416186 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2([CH2:12][C:13]([OH:15])=O)[NH:11][CH:10]=[CH:9][S:8]2)=[CH:3][CH:2]=1.[NH2:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=[O:20].C(Cl)CCl.CCN(C(C)C)C(C)C.ON1C2N=CC=CC=2N=N1>C(Cl)Cl>[CH:19]([C:18]1[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=1[NH:16][C:13](=[O:15])[CH2:12][C:7]1([C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)[NH:11][CH:10]=[CH:9][S:8]1)=[O:20]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 682552-AminobenzaldehydeHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 86610488HCID 86610488, compound

Product 1

HCID 86610489HCID 86610489, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In an oven-dried, 50-mL, round-bottomed flask were placed 2-(4-pyridyl)-thiazole acetic acid (Step b, 140 mg, 0.64 mmol), 2-aminobenzaldehyde (Aldrich, 270 mg, 2.22 mmol), EDC (Aldrich, 244 mg, 1.27 mmol), and DIEA (Aldrich, 148 mg, 0.20 mL, 1.15 mmol) in CH2Cl2 (20 mL). The mixture was cooled to 0° C., and 1-hydroxy-7-azabenzotriazole (Aldrich, 173 mg, 1.27 mmol) was added in one portion. The reaction was warmed to RT slowly, stirred for 12 h, and concentrated in vacuo. The resulting crude product was purified by flash chromatography (EtOAc/hexanes, 50:50) to afford N-(2-formylphenyl)-2-(4-pyridyl)-thiazole acetamide as a white solid. Mp: 136-137° C. MS m/z: 324 (M+1). Calc'd for C17H13N3O2S: 323.07.

Workup

  1. temperatureThe reaction was warmed to RT slowly
  2. concentrationconcentrated in vacuo
  3. customThe resulting crude product was purified by flash chromatography (EtOAc/hexanes, 50:50)

Sources & evidence

ORD record
ord-1801a2ac7d7d4118a93e47213a7f23fe
Source dataset
uspto-grants-2004_11
Patent number
US06822097B1

Reaction notes

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