Carbon Dioxide → HCID 10979471, compound

HRID 1707800Notes

Reaction equation

HRID 1707800 reaction equation
[CH2:1]([O:11][C:12]1[C:13](C(N[O-])=O)=[CH:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[Na+].C(=O)=O.C(#[N:32])C>>[CH2:1]([O:11][C:12]1[C:13]([NH2:32])=[CH:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 3

HCID 280Carbon DioxideHCID 6342AcetonitrileHCID 23681993HCID 23681993, compound

Product 1

HCID 10979471HCID 10979471, compoundYield 84%

Conditions

Temperature
60 °C

Procedure

Two liter of acetonitrile was added to 510 g of sodium 3-decyloxy-2-naphthalenehydroxamate obtained above, and stirred for about 30 minutes at 60° C. Thereupon, evolution of carbon dioxide gas was confirmed. The reaction mixture was further stirred with heating for 1 hour. Then, the insoluble matter (3,3'-didecyloxy-2-2'-dinaphthylurea) was filtered out, and the filtrate was concentrated. The residue was dissolved in 1 liter of ethyl acetate, and washed 3 times with 500 ml of water. The organic layer was separated from the aqueous layer, dried with Glauber's salt, and then concentrated. Thus, 323 g of whitish orange 3-decyloxy-2-naphthylamine (Compound 1) was obtained in a 84% yield. The melting point of the product was 64°-65.5° C.

Workup

  1. customobtained above, and
  2. stirringThe reaction mixture was further stirred
  3. temperaturewith heating for 1 hour
  4. filtrationThen, the insoluble matter (3,3'-didecyloxy-2-2'-dinaphthylurea) was filtered out
  5. concentrationthe filtrate was concentrated
  6. dissolutionThe residue was dissolved in 1 liter of ethyl acetate
  7. washwashed 3 times with 500 ml of water
  8. customThe organic layer was separated from the aqueous layer
  9. dry with materialdried with Glauber's salt
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d1db13db96dd437e91899c508542eb60
Source dataset
uspto-grants-1994_10
Patent number
US05354891

Reaction notes

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