Diethyl Ether → HCID 73177631, compound

HRID 1619738Notes

Reaction equation

HRID 1619738 reaction equation
[Cl:1]N1C(=O)CCC1=O.CN(C=O)C.[C:14]1([CH2:20][CH:21]=[N:22][OH:23])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OCC)C>O>[C:14]1([CH2:20][C:21]([Cl:1])=[N:22][OH:23])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6228Dimethylformamide2×HCID 31398ChlorosuccinimideHCID 99748Phenylacetaldoxime

Product 1

HCID 73177631HCID 73177631, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of N-chlorosuccinimide (3.25 g, 24 mmol) in abs. DMF (18 ml) was added to a solution of compound V (2.7 g, 20 mmol) in abs. DMF (12 ml) at a temperature of 30-40° C. within 20 min. Cooling in an ice bath was carried out if necessary. The reaction mixture was stirred for 3 h at RT and then mixed with diethyl ether (175 ml) and water (115 ml). The phases were separated and the aqueous phase was extracted with diethyl ether (2×75 ml). The combined organic extracts were washed successively with water (100 ml) and sat. NaCl solution (100 ml). The organic phase was dried and concentrated. Compound W was obtained as a yellowish-green oil (3.33 g) and immediately reacted further.

Workup

  1. temperatureCooling in an ice bath
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with diethyl ether (2×75 ml)
  4. washThe combined organic extracts were washed successively with water (100 ml) and sat. NaCl solution (100 ml)
  5. customThe organic phase was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-021c1d3f7d094ea7889fc1b69649d225
Source dataset
uspto-grants-2014_07
Patent number
US08772307B2

Reaction notes

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