Ethanol → HCID 70485863, compound

HRID 1248281Notes

Reaction equation

HRID 1248281 reaction equation
Br.[NH:2]1[CH2:6][CH2:5][N:4]=[C:3]1[CH:7]([O:9][C:10]1[C:11]([CH3:18])=[C:12]([NH2:17])[CH:13]=[CH:14][C:15]=1[CH3:16])[CH3:8].[C:19](Cl)(Cl)=[O:20].[CH2:23]([OH:25])[CH3:24]>C(#N)C.C1(C)C=CC=CC=1>[OH2:9].[NH:4]1[CH2:5][CH2:6][N:2]=[C:3]1[CH:7]([O:9][C:10]1[C:11]([CH3:18])=[C:12]([NH:17][C:19](=[O:20])[O:25][CH2:23][CH3:24])[CH:13]=[CH:14][C:15]=1[CH3:16])[CH3:8].[CH2:23]([O:25][C:19](=[O:20])[NH:17][C:12]1[CH:13]=[CH:14][C:15]([CH3:16])=[C:10]([O:9][CH:7]([C:3]2[NH:4][CH2:5][CH2:6][N:2]=2)[CH3:8])[C:11]=1[CH3:18])[CH3:24]

Participants

6

Reactant 3

HCID 702EthanolHCID 6371PhosgeneHCID 131714244HCID 131714244, compound

Product 1

HCID 70485863HCID 70485863, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of the title product of Example 7 (5.0 g, 15.9 mmole) in 130 ml of acetonitrile was added 13.8 ml (ca. 16 mmole) of 12% phosgene in toluene. After 18 hours 25 ml absolute ethanol was added, and the mixture was stirred for one hour. Volatiles were removed in vacuo and the residue was dissolved in water. After adjusting to pH 10 with dilute sodium hydroxide, the solution was extracted with two portions of diethyl ether, and the combined organic layers were washed with water, dried over magnesium sulfate, filtered, and concentrated in vacuo. The solid that crystallized during the concentration was triturated with diethyl ether and collected by filtration to give 2.2 g of the title compound as the hemihydrate. Structure assignment was supported by nmr and infrared spectra and by elemental analysis.

Workup

  1. customVolatiles were removed in vacuo
  2. dissolutionthe residue was dissolved in water
  3. extractionthe solution was extracted with two portions of diethyl ether
  4. washthe combined organic layers were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe solid that crystallized during the concentration
  9. customwas triturated with diethyl ether
  10. filtrationcollected by filtration

Sources & evidence

ORD record
ord-b1c031afe35749fa9c891cb27694ab92
Source dataset
uspto-grants-1985_06
Patent number
US04523020

Reaction notes

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