Triphenylphosphine → 3-Methyl-5-[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]propyl]-1,2,4-thiadiazole

HRID 399505Notes

Reaction equation

HRID 399505 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[S:9][N:8]=[C:7]([CH3:10])[N:6]=1.[CH3:11][C:12]1[O:16][N:15]=[C:14]([C:17]2[CH:22]=[C:21]([CH3:23])[C:20](O)=[C:19]([CH3:25])[CH:18]=2)[N:13]=1.CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:10][C:7]1[N:6]=[C:5]([CH2:4][CH2:3][CH2:2][O:1][C:20]2[C:19]([CH3:25])=[CH:18][C:17]([C:14]3[N:13]=[C:12]([CH3:11])[O:16][N:15]=3)=[CH:22][C:21]=2[CH3:23])[S:9][N:8]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 189678815-(3-Hydroxypropyl)-3-methyl-1,2,4-thiadiazoleHCID 1354490044-(5-Methyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenol

Product 1

HCID 189678713-Methyl-5-[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]propyl]-1,2,4-thiadiazoleYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 5-(3-hydroxypropyl)-3-methyl-1,2,4-thiadiazole (66 mg, 0.42 mmol), 4-(5-methyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenol (94 mg, 0.46 mmol), and DEAD (80 mg, 0.46 mmol) was dissolved in 5 mL of THF. To the above solution was added triphenylphosphine (120 mg, 0.46 mmol) at 0° C. and the mixture was allowed to warm to 20° C. overnight. The solvent was removed in vacuo, an aqueous sodium bicarbonate solution was added, and the mixture was extracted with methylene chloride (3×). The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica column chromatography (20 cm column, ethyl acetate/hexane, from 1/6 to 1/4) followed by recrystallization from ethyl acetate/hexane to afford 88 mg (61%) of 3-methyl-5-[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)-2,6 -dimethylphenoxy]propy]-1,2,4-thiadiazole, as a white crystalline solid, m.p. 67°--71° C.

Workup

  1. customThe solvent was removed in vacuo
  2. additionan aqueous sodium bicarbonate solution was added
  3. extractionthe mixture was extracted with methylene chloride (3×)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica column chromatography (20 cm column, ethyl acetate/hexane, from 1/6 to 1/4)
  7. customfollowed by recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-8f4878c8e2134a1bbd04fb374fa047a5
Source dataset
uspto-grants-1998_10
Patent number
US05821257

Reaction notes

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