Chloroacetaldehyde → HCID 58257806, compound

HRID 2075732Notes

Reaction equation

HRID 2075732 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([S:18][C:19]3[CH:20]=[C:21]([C:25]([OH:30])([CH2:28][CH3:29])[CH2:26][CH3:27])[CH:22]=[CH:23][CH:24]=3)=[CH:7][CH:8]=2)[N:3]=1.Cl[CH2:32][CH:33]=O.C(=O)(O)[O-].[Na+].O>O1CCOCC1>[C:12]1([C:10]2[C:9]3[C:4](=[CH:5][C:6]([S:18][C:19]4[CH:20]=[C:21]([C:25]([OH:30])([CH2:28][CH3:29])[CH2:26][CH3:27])[CH:22]=[CH:23][CH:24]=4)=[CH:7][CH:8]=3)[N:3]3[CH:32]=[CH:33][N:1]=[C:2]3[CH:11]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 33ChloroacetaldehydeHCID 962WaterHCID 516892Sodium BicarbonateHCID 58257762HCID 58257762, compound

Product 1

HCID 58257806HCID 58257806, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To 10q (200 mg, 0.48 mmol) in 1,4-dioxane (4 mL) was added chloroacetaldehyde (0.07 mL, 0.53 mmol), sodium bicarbonate (243 mg, 2.89 mmol), and water (2 mL). The mixture was heated to 80° C. for 5 hours, and then cooled to room temperature and concentrated. The residue was purified by silica gel chromatography (30% EtOAc in hexanes) to give the desired product, 10r.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel chromatography (30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-0bc52774f04c4febb69895c701cfea08
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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