Triethylamine → HCID 14407629, compound

HRID 621470Notes

Reaction equation

HRID 621470 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([NH2:13])[CH:10]=[CH:11][CH:12]=2)=[N:4][N:3]=1.C(N(CC)CC)C.[CH3:21][C:22]1[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][C:23]=1[O:24][CH2:25][CH2:26][CH2:27][C:28]([CH3:33])([CH3:32])[C:29](Cl)=[O:30]>ClCCl.C(OCC)(=O)C>[CH3:21][C:22]1[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][C:23]=1[O:24][CH2:25][CH2:26][CH2:27][C:28]([CH3:33])([CH3:32])[C:29]([NH:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:5]2[O:6][C:2]([CH3:1])=[N:3][N:4]=2)[CH:8]=1)=[O:30]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 144076195-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoyl chlorideHCID 144076283-(5-Methyl-(1,3,4)oxadiazol-2-yl)-phenylamine

Product 1

HCID 14407629HCID 14407629, compoundYield 7.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7.05 g (0.04 mol) of 3-(5-methyl-1,3,4-oxadiazol-2-yl)benzenamine and 10 ml of triethylamine in 300 ml of dichloromethane is added 11 g of 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoyl chloride (U.S. Pat. No. 4,285,951). The mixture is worked up, the crude product slurried in ethyl acetate and filtered through silica gel. The solvent is evaporated to give 1.2 g of 5-(2,5-dimethylphenoxy)-2,2-dimethyl-N-[3-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]pentanamide after recrystallization from 2-propanol; mp 90°-92° C.

Workup

  1. filtrationfiltered through silica gel
  2. customThe solvent is evaporated

Sources & evidence

ORD record
ord-2a39bc44a2bc45b28a5a1ae0b377da98
Source dataset
uspto-grants-1989_04
Patent number
US04824843

Reaction notes

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