Chlorodifluoromethane → HCID 9943956, compound

HRID 1744034Notes

Reaction equation

HRID 1744034 reaction equation
[CH:1](=[N:8][CH:9]([CH2:15][CH2:16][C:17]#[N:18])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[Li+].Cl[CH:26]([F:28])[F:27]>O1CCCC1>[CH:1](=[N:8][C:9]([CH:26]([F:28])[F:27])([CH2:15][CH2:16][C:17]#[N:18])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6372ChlorodifluoromethaneHCID 11207281HCID 11207281, compoundHCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)

Product 1

HCID 9943956HCID 9943956, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To the solution of crude ethyl 2-benzylideneamino-4-cyanobutyrate (4) obtained above, was added 0.35 L of tetrahydrofuran (THF) and 28.0 g of lithium t-butoxide (1.6 eq) at 5° C. The mixture was stirred at ˜5° C. for 0.5 h, at 20–25° C. for 2 h, and then warmed to 40° C. Chlorodifluoromethane (34.2 g, 1.8 eq) was slowly bubbled into the reaction mixture, and the temperature maintained at 40–50° C. When the exotherm subsided, bubbling was continued for another ˜15 min. and then stopped. The reaction mixture was stirred at 40° C. for 1–2 h. After the reaction was complete, the solvent was removed under reduced pressure. The crude product 5 was ready for use in the next step.

Workup

  1. temperaturewarmed to 40° C
  2. temperaturethe temperature maintained at 40–50° C
  3. custombubbling
  4. waitwas continued for another ˜15 min.
  5. stirringThe reaction mixture was stirred at 40° C. for 1–2 h
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e1fe9d5a518c45f2ae56f30158c88c9c
Source dataset
uspto-grants-2006_03
Patent number
US07012158B2

Reaction notes

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