Water → HCID 54514258, compound

HRID 1658560Notes

Reaction equation

HRID 1658560 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:4]=1[CH2:5][O:6][C:7]([NH:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1)=[O:8].C(Cl)(=O)C(Cl)=O.[CH2:31]([O:33][CH:34](O)[CH3:35])[CH3:32].O>C1COCC1.CN(C=O)C.N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:4]=1[CH2:5][O:6][C:7]([NH:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([O:16][CH2:32][CH2:31][O:33][CH2:34][CH3:35])=[O:15])=[CH:12][CH:11]=1)=[O:8]

Participants

8

Reactant 4

HCID 962WaterHCID 65578Oxalyl chlorideHCID 101298981-EthoxyethanolHCID 2152801738618-47-2

Product 1

HCID 54514258HCID 54514258, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(2,5-dimethoxybenzyloxy-carbonyl)-para-aminobenzoic acid (3.31g) in dry THF (30ml) was treated with oxalyl chloride (1.65g) and one drop of dry DMF. After 0.5 hour the reaction had subsided and the acid chloride solution was added dropwise to a stirred solution of ethoxyethanol (1.2g) in dry pyridine, then poured into water (ca 250ml) and the crude product extracted into ether. The ether was washed with 1N HCl 1N NaOH, water and dried with Mg SO4. The solvent was concentrated in vacuo leaving a yellow oil.

Workup

  1. extractionthe crude product extracted into ether
  2. washThe ether was washed with 1N HCl 1N NaOH, water
  3. dry with materialdried with Mg SO4
  4. concentrationThe solvent was concentrated in vacuo
  5. customleaving a yellow oil

Sources & evidence

ORD record
ord-4f9d0700c9c845988d4d0344485d408a
Source dataset
uspto-grants-1976_06
Patent number
US03965144

Reaction notes

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