Thionyl Chloride → HCID 18799436, compound

HRID 1637624Notes

Reaction equation

HRID 1637624 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[C:7]([CH2:18]O)=[N:8][CH:9]=[CH:10][C:11]=1[N:12]([CH3:17])[CH2:13][CH2:14][CH2:15][OH:16]>ClCCl>[Cl:5][C:6]1[C:7]([CH2:18][Cl:3])=[N:8][CH:9]=[CH:10][C:11]=1[N:12]([CH3:17])[CH2:13][CH2:14][CH2:15][OH:16]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 18799400HCID 18799400, compound

Product 1

HCID 18799436HCID 18799436, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thionyl chloride (3.5 ml, 47.6 mmol), dissolved in dichloromethane (25 ml), is added dropwise at 4° C. to a solution of 3-[(3-chloro-2-hydroxymethyl-pyridin-4-yl)-methyl-amino]-propanol (5.0 g, 21.6 mmol) in dichloromethane (75 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 vacua. 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 vacua
  7. customThe residue is employed without additional purification for the synthesis

Sources & evidence

ORD record
ord-e43959ba0da54d44bc843f5288d32ab8
Source dataset
uspto-grants-2000_03
Patent number
US06043242

Reaction notes

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