Ethanol → HCID 178466247, compound

HRID 1088460Notes

Reaction equation

HRID 1088460 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=3)[O:17][CH:18]([CH3:21])[C:19]#[N:20])=[N:9]2)=[CH:4][CH:3]=1.C([Sn]([N:38]=[N+:39]=[N-:40])(CCCC)CCCC)CCC.C(OCC)C.C(O)C>C(Cl)Cl.C(O)(=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=3)[O:17][CH:18]([C:19]3[NH:40][N:39]=[N:38][N:20]=3)[CH3:21])=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 3283Diethyl EtherHCID 4984872Tributyltin azideHCID 53923850HCID 53923850, compound

Product 1

HCID 178466247HCID 178466247, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of the propanonitrile (110 g) from Step 2 and tri-butyltin azide (120 g) was heated at 130° for 3 hours. The residue was dissolved in CH2Cl2 (1 L) on a steam bath. This solution was added to a mixture of diethylether (2 L), ethanol (100 ml) and acetic acid (10 ml). This mixture was evaporated under vacuo to approximately 300 ml. The residue was triturated with ether (1.5 L), ethyl acetate (600 ml) and filtered. The yellow solid was dissolved in 2 N NaOH (150 ml) and H2O (1 L). The aqueous solution was extracted with ethyl acetate (100 ml). The aqueous solution was then acidified with AcOH (100 ml) in ethyl acetate (100 ml). The mixture was stirred 30 min and filtered to give title compound. m.p. 100°-103°.

Workup

  1. temperaturewas heated at 130° for 3 hours
  2. customThis mixture was evaporated under vacuo to approximately 300 ml
  3. customThe residue was triturated with ether (1.5 L), ethyl acetate (600 ml)
  4. filtrationfiltered
  5. dissolutionThe yellow solid was dissolved in 2 N NaOH (150 ml)
  6. extractionThe aqueous solution was extracted with ethyl acetate (100 ml)
  7. filtrationfiltered

Sources & evidence

ORD record
ord-011db7bab04f453ea65179e83847b3e4
Source dataset
uspto-grants-1990_10
Patent number
US04962203

Reaction notes

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