Ammonium Chloride → HCID 21843577, compound

HRID 1941301Notes

Reaction equation

HRID 1941301 reaction equation
Br[C:2]1[S:6][CH:5]=[N:4][CH:3]=1.[CH2:7]([Li])[CH2:8][CH2:9][CH3:10].C(C1C=C[C:17]([CH:20](C2C=CC(F)=CC=2)[CH2:21][C:22]([CH2:24][CH:25]([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)C2C=CC(C#N)=CC=2)=[O:23])=CC=1)#N.[Cl-].[NH4+:49]>C(OCC)C>[C:7]([C:8]1[CH:17]=[CH:20][C:21]([C:22]([C:2]2[S:6][CH:5]=[N:4][CH:3]=2)([OH:23])[CH2:24][CH2:25][C:34]2[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=2)=[CH:10][CH:9]=1)#[N:49]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 5460595-BromothiazoleHCID 67577237HCID 67577237, compoundHCID 178418339Butyllithium

Product 1

HCID 21843577HCID 21843577, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

5-bromothiazole (1.66 g, 10 mmol) is dissolved in diethyl ether. n-Butyllithium (4.85 ml, 2.5M) is added very slowly under nitrogen atmosphere at -60° C. After stirring for 20 minutes at -60° C. (4-cyanophenyl)-2-(4-fluorophenyl)ethyl ketone (2.5 g, 10 mmol) is added in diethyl ether at the same temperature and the stirring is continued for another 2 hours. The reaction mixture is allowed to warm to room temperature after which it is decomposed with saturated ammonium chloride solution. The diethyl ether layer is separated and the solvent is evaporated. Water is added and the product is extracted into ethyl acetate. After drying and evaporation of the solvent the residue is mixed with ethanol and the black precipitate is filtered off. The ethanol is evaporated and the product is purified by flash chromatography (eluent: dichloromethane/methanol 46:1).

Workup

  1. customThe diethyl ether layer is separated
  2. customthe solvent is evaporated
  3. additionWater is added
  4. extractionthe product is extracted into ethyl acetate
  5. customAfter drying
  6. customevaporation of the solvent the residue
  7. additionis mixed with ethanol
  8. filtrationthe black precipitate is filtered off
  9. customThe ethanol is evaporated
  10. customthe product is purified by flash chromatography (eluent: dichloromethane/methanol 46:1)

Sources & evidence

ORD record
ord-58eddc2c99f0474ab799e59cd8fa90e9
Source dataset
uspto-grants-1997_12
Patent number
US05703109

Reaction notes

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