Chloroacetaldehyde → HCID 11667810, compound

HRID 2235010Notes

Reaction equation

HRID 2235010 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[O:5][CH:6]1[CH2:12][CH:11]2[N:13]([CH2:14][C:15]([NH2:17])=[S:16])[CH:8]([CH2:9][CH2:10]2)[CH2:7]1.Cl[CH2:23][CH:24]=O>C(O)(=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[O:5][CH:6]1[CH2:12][CH:11]2[N:13]([CH2:14][C:15]3[S:16][CH:23]=[CH:24][N:17]=3)[CH:8]([CH2:9][CH2:10]2)[CH2:7]1

Participants

5

Reactant 2

HCID 33ChloroacetaldehydeHCID 11631574HCID 11631574, compound

Product 1

HCID 11667810HCID 11667810, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

to 2-[3-(3,4-Dichloro-phenoxy)-8-aza-bicyclo[3.2.1]oct-8-yl]-thioacetamide (0.5 g) in 5 ml of acetic acid was added 0.13 g of 50% chloroacetaldehyde in water. The reaction mixture was stirred at reflux overnight and cooled to room temperature and poured into 50 ml of water. The mixture was extracted twice with dichloromethane. The organic phase was dried with magnesium sulphate and evaporated to and oil. The product was isolated by column chromatography with dichloromethane/methanol (9:1) with 1% ammonia as eluent, the product fractions was evaporated to dryness. Yield 0.1 g (19%). Mp. 123-124° C.

Workup

  1. temperatureat reflux overnight
  2. extractionThe mixture was extracted twice with dichloromethane
  3. dry with materialThe organic phase was dried with magnesium sulphate
  4. customevaporated to and oil
  5. customThe product was isolated by column chromatography with dichloromethane/methanol (9:1) with 1% ammonia as eluent
  6. customthe product fractions was evaporated to dryness

Sources & evidence

ORD record
ord-713e794d8e104a99b415333117005595
Source dataset
uspto-grants-2010_05
Patent number
US07713990B2

Reaction notes

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