Ammonium Chloride → HCID 67463357, compound

HRID 1620000Notes

Reaction equation

HRID 1620000 reaction equation
[Cu][C:2]#N.C[Li].[Cl-].C([Al+]CC)C.[O:12]=[C:13]([C:21]1[CH:34]=[CH:33][C:24]2[N:25]=[C:26]([C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)[O:27][C:23]=2[CH:22]=1)/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17].[Cl-].[NH4+]>C1COCC1.CCCCCC>[CH3:2][CH:15]([CH2:14][C:13](=[O:12])[C:21]1[CH:34]=[CH:33][C:24]2[N:25]=[C:26]([C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)[O:27][C:23]=2[CH:22]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 16686102Diethyl aluminum chlorideHCID 86689072HCID 86689072, compoundHCID 178418348HCID 178418348, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 67463357HCID 67463357, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
-5 °C

Procedure

5 ml THF are added to 110 mg (1.23 mmol) copper-(I)-cyanide, the suspension is cooled to −5° C., then 770 μl (1.23 mmol) 1.6M methyl lithium dissolved in THF are added dropwise at a maximum temperature of 0° C., the mixture is stirred for 45 min, then cooled to −70° C. 1.23 ml (1.23 mmol) 1M diethyl aluminium chloride dissolved in hexane are then added dropwise to the reaction mixture, it is stirred for 25 min at −70° C., then are 100 mg (0.31 mmol) ethyl (E)-4-oxo-4-(2-thiophen-2-yl-benzoxazol-6-yl)-but-2-enoate dissolved in 5 ml THF are added dropwise. The reaction solution is then added to sat. ammonium chloride solution and extracted with diethyl ether. The org. phase is concentrated by rotary evaporation i. V. and the residue is purified by RP-HPLC.

Workup

  1. additionare added dropwise at a maximum temperature of 0° C.
  2. temperaturecooled to −70° C
  3. additionare then added dropwise to the reaction mixture, it
  4. stirringis stirred for 25 min at −70° C.
  5. additionare added dropwise
  6. extractionextracted with diethyl ether
  7. concentrationphase is concentrated by rotary evaporation i
  8. customand the residue is purified by RP-HPLC

Sources & evidence

ORD record
ord-8823fefe1869414bb2879b2bb545fb77
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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