Diethyl Ether → HCID 73083080, compound

HRID 1619741Notes

Reaction equation

HRID 1619741 reaction equation
[Cl:1]N1C(=O)CCC1=O.CN(C=O)C.[C:14]1([CH2:20][CH2:21][CH:22]=[N:23][OH:24])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OCC)C>O>[C:14]1([CH2:20][CH2:21][C:22]([Cl:1])=[N:23][OH:24])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6228Dimethylformamide2×HCID 31398ChlorosuccinimideHCID 51631601197-50-8

Product 1

HCID 73083080HCID 73083080, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of N-chlorosuccinimide (2.24 g, 16.6 mmol) in abs. DMF (11 ml) was added to a solution of compound Z (2.06 g, 13.8 mmol) in abs. DMF (10 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 (120 ml) and water (80 ml). The phases were separated. The aqueous phase was extracted with diethyl ether (2×50 ml). The combined organic extracts were washed successively with water (80 ml) and sat. NaCl solution (100 ml). The organic phase was dried and concentrated. 3-phenyl propanehydroximoyl chloride was obtained as a light green oil (2.47 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 (2×50 ml)
  4. washThe combined organic extracts were washed successively with water (80 ml) and sat. NaCl solution (100 ml)
  5. customThe organic phase was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9a1a9cb89dfe439a861ef2e5bfc58215
Source dataset
uspto-grants-2014_07
Patent number
US08772307B2

Reaction notes

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