Benzyl Chloride → HCID 14716816, compound

HRID 569211Notes

Reaction equation

HRID 569211 reaction equation
[CH3:1][C:2]([NH:5][C:6]([C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:7])([CH3:4])[CH3:3].[Br-].[Na+].C([Li])CCC.[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1.O>[C:23]1([CH2:22][CH2:14][C:13]2[C:8]([C:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 7503Benzyl ChlorideHCID 253881Sodium BromideHCID 5463796N-tert-Butyl-3-methylpyridine-2-carboxamideHCID 178418339Butyllithium2×

Product 1

HCID 14716816HCID 14716816, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

Tetrahydrofuran (125 mL), N-(1,1-dimethylethyl)-3-methyl-2-pyridine carboxamide (1 equivalent) and sodium bromide (1.3 g) are charged and cooled to -40° C. under nitrogen. Two equivalents of n-butyllithium are then added over 40 minutes. When half the n-butyllithium is added the mixture turns purple. Benzyl chloride (1.05 equivalents) is then added dropwise (1:1 solution in tetrahydrofuran) over 40-50 minutes while the temperature is maintained at -40° C. After 30 minutes at -40° C., the mixture is diluted with water (250 ml) and the organic phase separated. This phase is dried over sodium sulphate and the solvent removed yielding an oil from which solid product may crystallize. Product yield of 94% determined by internal standard assay on gas chromatograph.

Workup

  1. temperatureis maintained at -40° C
  2. customthe organic phase separated
  3. dry with materialThis phase is dried over sodium sulphate
  4. customthe solvent removed
  5. customyielding an oil from which solid product
  6. custommay crystallize

Sources & evidence

ORD record
ord-5865e0f1508248c39f9f2b3fae5a0b21
Source dataset
uspto-grants-1988_03
Patent number
US04731447

Reaction notes

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