Dichloromethane → 5-Morpholin-4-ylmethyl-furan-2-carbonyl chloride hydrochloride

HRID 1452760Notes

Reaction equation

HRID 1452760 reaction equation
[ClH:1].[N:2]1([CH2:8][C:9]2[O:13][C:12]([C:14](O)=[O:15])=[CH:11][CH:10]=2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.C(Cl)[Cl:18]>S(Cl)(Cl)=O.CN(C=O)C>[ClH:18].[N:2]1([CH2:8][C:9]2[O:13][C:12]([C:14]([Cl:1])=[O:15])=[CH:11][CH:10]=2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 53313615-((Morpholin-4-yl)methyl)furan-2-carboxylic acid hydrochloride

Product 1

HCID 866001495-Morpholin-4-ylmethyl-furan-2-carbonyl chloride hydrochlorideYield 83%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 24386Thionyl ChlorideSolvent

Procedure

A suspension of 5-morpholin-4-ylmethyl-furan-2-carboxylic acid hydrochloride in thionyl chloride with 2 drops of DMF was refluxed under N2 for 3 hours, then cooled to room temperature. Dry CH2Cl2 was added and solvents were evaporated in vacuo. The residue was triturated with dry CH2Cl2, and the resulting solid was filtered, washed with dry CH2Cl2 and dried in vacuo to give 373 mg (83% yield) of 5-morpholin-4-ylmethyl-furan-2-carbonyl chloride hydrochloride as a white solid. 1H-NMR (d6-DMSO) δ: 11.54 (broad s, 1H), 7.26 (d, 1H), 6.92 (d, 1H), 4.49 (s, 2H), 3.94 (m, 2H), 3.74 (m, 2H), 3.28 (m, 2H), 3.09 (broad s, 2H).

Workup

  1. temperaturewas refluxed under N2 for 3 hours
  2. customsolvents were evaporated in vacuo
  3. customThe residue was triturated with dry CH2Cl2
  4. filtrationthe resulting solid was filtered
  5. washwashed with dry CH2Cl2
  6. customdried in vacuo

Sources & evidence

ORD record
ord-6242b48cce774f7db40312558493922e
Source dataset
uspto-grants-2009_01
Patent number
US07473783B2

Reaction notes

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