Chloroacetyl chloride → HCID 58371903, compound

HRID 1020956Notes

Reaction equation

HRID 1020956 reaction equation
[CH3:1][N:2]1[CH:6]=[N:5][C:4]([C:7]2[S:11][C:10]([C:12]3[CH2:13][CH2:14][NH:15][CH2:16][CH:17]=3)=[CH:9][CH:8]=2)=[N:3]1.[Cl:18][CH2:19][C:20](Cl)=[O:21]>ClCCl>[Cl:18][CH2:19][C:20]([N:15]1[CH2:14][CH:13]=[C:12]([C:10]2[S:11][C:7]([C:4]3[N:5]=[CH:6][N:2]([CH3:1])[N:3]=3)=[CH:8][CH:9]=2)[CH2:17][CH2:16]1)=[O:21]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 58371870HCID 58371870, compound

Product 1

HCID 58371903HCID 58371903, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of 4-[5-(1-methyl-1H-[1,2,4]triazol-3-yl)-thiophen-2-yl]-1,2,3,6-tetrahydro-pyridine (7BW) (1.5 g, 4.72 mmol) in dichloromethane (50 ml) was added TEA (4.5 ml, 28.32 mmol) dropwise. After stirred at 0° C. for 10 min, chloroacetyl chloride (1.12 ml, 14.2 mmol) was added to the reaction mixture. The resulting mixture was stirred at 0° C. for 1 hr., and quenched with water (15.6 ml). The reaction mixture was diluted with dichloromethane (200 ml). The organic layer was separated and washed with brine, dried over MgSO4. Reaction mixture was concentrated to ˜50 ml, ether was added and the solid was filtered out to get the desired product (8BW).

Workup

  1. stirringThe resulting mixture was stirred at 0° C. for 1 hr
  2. custom, and quenched with water (15.6 ml)
  3. additionThe reaction mixture was diluted with dichloromethane (200 ml)
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. customReaction mixture
  8. concentrationwas concentrated to ˜50 ml, ether
  9. additionwas added
  10. filtrationthe solid was filtered out

Sources & evidence

ORD record
ord-93f9162993b2417c85c1a38c7342e5f3
Source dataset
uspto-grants-2014_05
Patent number
US08716483B2

Reaction notes

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