Toluene → HCID 19900669, compound

HRID 1029528Notes

Reaction equation

HRID 1029528 reaction equation
[C:1](Cl)(Cl)=[O:2].C1(C)C=CC=CC=1.[CH3:12][C:13]([C:16]1[CH:17]=[C:18]([S:27][CH2:28][CH2:29][C:30]([NH:32][NH2:33])=[O:31])[CH:19]=[C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:21]=1[OH:22])([CH3:15])[CH3:14].C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:15][C:13]([C:16]1[CH:17]=[C:18]([S:27][CH2:28][CH2:29][C:30]2[O:31][C:1](=[O:2])[NH:33][N:32]=2)[CH:19]=[C:20]([C:23]([CH3:24])([CH3:25])[CH3:26])[C:21]=1[OH:22])([CH3:12])[CH3:14]

Participants

7

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 516892Sodium BicarbonateHCID 19609556HCID 19609556, compound

Product 1

HCID 19900669HCID 19900669, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 12.5% solution of phosgene in toluene (5.5 mL, 6.2 mmol) is added dropwise to a -78° C. solution of 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]propanoic acid hydrazide (1.0 g, 2.94 mmol) in tetrahydrofuran (100 mL). The reaction mixture is stirred for 10 minutes then poured into a separatory funnel containing ethyl acetate and aqueous sodium bicarbonate. The organic phase is washed three times with water and once with brine. Drying the organic phase over magnesium sulfate and evaporation gives a heavy oil which is chromatographed on a 100 g column of silica with methanol/chloroform (3/97). After coevaporation with dichloromethane the product solidifies affording 0.64 g (63%) of 5-[2-[[3,5-bis-(1,1-dimethylethyl)-4-hydroxyphenyl]thio]ethyl]-1,3,4-oxadiazol-2(3H)-one, mp 86.0°-87.5° C.

Workup

  1. additionthen poured into a separatory funnel
  2. washThe organic phase is washed three times with water
  3. customDrying the organic phase
  4. customover magnesium sulfate and evaporation
  5. customgives a heavy oil which
  6. customis chromatographed on a 100 g column of silica with methanol/chloroform (3/97)

Sources & evidence

ORD record
ord-f0df82ba6c944bb9b0675adadf1c6063
Source dataset
uspto-grants-1992_04
Patent number
US05102897

Reaction notes

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