Thionyl Chloride → HCID 68182138, compound

HRID 1620238Notes

Reaction equation

HRID 1620238 reaction equation
O[CH2:2][C:3]1[C:4]([NH:15][CH2:16][CH2:17][NH:18][C:19](=[O:21])[CH3:20])=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH3:14])=[CH:8][CH:7]=2.O=S(Cl)[Cl:24]>C(Cl)Cl>[ClH:24].[Cl:24][CH2:2][C:3]1[C:4]([NH:15][CH2:16][CH2:17][NH:18][C:19](=[O:21])[CH3:20])=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH3:14])=[CH:8][CH:7]=2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68182226HCID 68182226, compound2×

Product 1

HCID 68182138HCID 68182138, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-(2-((3-(hydroxymethyl)-6-methoxyquinolin-2-yl)amino)ethyl)acetamide SLA 41088 (113 mg, 391 μmol) in dry CH2Cl2 (20 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (0.28 mL, 3.86 mmol). The mixture was stirred for 1.5 h at RT then concentrated to dryness at 40° C. under vacuum. The residue was then taken up in CH2Cl2 (20 mL) before concentration back to dryness at 40° C. under vacuum (done 3 times) to give N-(2-((3-(chloromethyl)-6-methoxyquinolin-2-yl)amino)ethyl)acetamide hydrochloride SLA 41090 as a yellow solid (135 mg, 100% yield).

Workup

  1. concentrationthen concentrated to dryness at 40° C. under vacuum
  2. concentrationThe residue was then taken up in CH2Cl2 (20 mL) before concentration back to dryness at 40° C. under vacuum (done 3 times)

Sources & evidence

ORD record
ord-863146690f694f02b8c7e47f8863077c
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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