Dichloromethane → HCID 22054208, compound

HRID 1830278Notes

Reaction equation

HRID 1830278 reaction equation
C(Cl)(=O)C(Cl)=O.C(Cl)Cl.[CH3:10][O:11][C:12]1[C:13](=[O:40])[C:14]([CH3:39])=[C:15]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[C:26]([CH:30]=2)[C:27](O)=[O:28])[C:16](=[O:20])[C:17]=1[O:18][CH3:19].[NH:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1>C1COCC1>[CH3:10][O:11][C:12]1[C:13](=[O:40])[C:14]([CH3:39])=[C:15]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([O:31][CH2:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[C:26]([CH:30]=2)[C:27]([N:41]2[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)=[O:28])[C:16](=[O:20])[C:17]=1[O:18][CH3:19]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8083MorpholineHCID 65578Oxalyl chlorideHCID 22054329HCID 22054329, compound

Product 1

HCID 22054208HCID 22054208, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Oxalyl chloride (0.150 g, 1.18 mmol) was added to a methylene chloride solution (5 ml) of 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-benzyloxybenzoic acid (0.050 g, 0.118 mmol) and the resulting solution was stirred at room temperature for 1 hour. The reaction solution was concentrated and after adding a THF solution of morpholine (0.036 g, 0.414 mmol) to the obtained residue, the solution was stirred at room temperature for 30 minutes. The reaction solution was poured into ice water and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (hexand:ethyl acetate=1:1) to obtain the titled compound (0.058 g, 0.117 mmol, 99%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. stirringthe solution was stirred at room temperature for 30 minutes
  3. extractionextracted with methylene chloride
  4. washThe extract was washed with water
  5. customdried
  6. customthe solvent was removed by distillation
  7. customThe obtained residue was purified by preparative thin-layer chromatography (hexand:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-d3a3e1809a744fa9b854b1a108b1980f
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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