Thionyl Chloride → 2-[(3-Chloro-2-chloromethyl-pyridin-4-yl)-methyl-amino]-ethanol

HRID 1637622Notes

Reaction equation

HRID 1637622 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[C:7]([CH2:17]O)=[N:8][CH:9]=[CH:10][C:11]=1[N:12]([CH3:16])[CH2:13][CH2:14][OH:15]>ClCCl>[Cl:5][C:6]1[C:7]([CH2:17][Cl:3])=[N:8][CH:9]=[CH:10][C:11]=1[N:12]([CH3:16])[CH2:13][CH2:14][OH:15]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 537528042-[(3-Chloro-2-hydroxymethyl-pyridin-4-yl)-methylamino]-ethanol

Product 1

HCID 543658082-[(3-Chloro-2-chloromethyl-pyridin-4-yl)-methyl-amino]-ethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thionyl chloride (7.4 ml, 101.5 mmol), dissolved in dichloromethane (50 ml), is added dropwise at 4° C. to a solution of (2-[(3-chloro-2-hydroxymethyl-pyridin-4-yl)-methylamino]-ethanol (10.0 g, 46.1 mmol) in dichloromethane (150 ml). The solution is stirred for 1 h at this temperature, triturated with ice water and neutralized with saturated sodium bicarbonate solution. After separation of the organic layer the aqueous phase is extracted with dichloromethane. The combined organic extracts are washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue is employed without additional purification for the synthesis described in step b).

Workup

  1. customtriturated with ice water and neutralized with saturated sodium bicarbonate solution
  2. customAfter separation of the organic layer the aqueous phase
  3. extractionis extracted with dichloromethane
  4. washThe combined organic extracts are washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue is employed without additional purification for the synthesis

Sources & evidence

ORD record
ord-9ac5451a145a4c1aa3d52696820f22b5
Source dataset
uspto-grants-2000_03
Patent number
US06043242

Reaction notes

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