Triethylamine → HCID 5273051, compound

HRID 1681911Notes

Reaction equation

HRID 1681911 reaction equation
ClN1C(=O)CCC1=O.[CH:9]1([CH:12]=[N:13][OH:14])[CH2:11][CH2:10]1.[CH3:15][C:16]1[CH:17]=[C:18]([C:29]2[N:33]=[C:32]([CH3:34])[O:31][N:30]=2)[CH:19]=[C:20]([CH3:28])[C:21]=1[O:22][CH2:23][CH2:24][CH2:25][C:26]#[CH:27].C(N(CC)CC)C>CN(C)C=O.N1C=CC=CC=1>[CH:9]1([C:12]2[CH:27]=[C:26]([CH2:25][CH2:24][CH2:23][O:22][C:21]3[C:16]([CH3:15])=[CH:17][C:18]([C:29]4[N:33]=[C:32]([CH3:34])[O:31][N:30]=4)=[CH:19][C:20]=3[CH3:28])[O:14][N:13]=2)[CH2:11][CH2:10]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 47893Cyclopropanecarboxaldehyde, oximeHCID 10107170HCID 10107170, compound

Product 1

HCID 5273051HCID 5273051, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6228DimethylformamideSolvent3×

Procedure

Following a procedure similar to that described in Example 2(b) and using 0.52 g N-chlorosuccinimide in 5 mls dimethylformamide, two drops of pyridine, 0.33 g cyclopropanecarboxaldehyde oxime from part (a) above in 10 mls dimethylformamide, 0.53 g 3-[3,5-dimethyl-4-(3-ethinylpropoxy)phenyl]-5-methyl-1,2,4-oxadiazole prepared by a procedure similar to that described in Example 1(b), and 0.40 g triethylamine in 20 mls dimethylformamide, there was obtained after chroamtography (MPLC, silica gel; 20:80 ethyl acetate/hexane) and recrystallization (methyl alcohol) 0.312 g of the title compound, m.p. 50.5°-51° C.

Workup

  1. customprepared by a procedure similar to
  2. customthere was obtained
  3. customafter chroamtography (MPLC, silica gel; 20:80 ethyl acetate/hexane) and recrystallization (methyl alcohol) 0.312 g of the title compound, m.p. 50.5°-51° C.

Sources & evidence

ORD record
ord-50feeb11a3fa423d950eeb3e53065a09
Source dataset
uspto-grants-1992_12
Patent number
US05175177

Reaction notes

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