Thioacetic acid → HCID 59226264, compound

HRID 1483834Notes

Reaction equation

HRID 1483834 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O.O[CH:33]1[CH2:38][CH2:37][CH:36]([N:39]2[C:47](=[O:48])[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:40]2=[O:49])[CH2:35][CH2:34]1.[CH3:50][C:51]([SH:53])=[O:52]>C1COCC1.O.CC(=O)OCC>[C:51](=[O:52])([S:53][CH:33]1[CH2:38][CH2:37][CH:36]([N:39]2[C:47](=[O:48])[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:40]2=[O:49])[CH2:35][CH2:34]1)[CH3:50]

Participants

8

Reactant 4

HCID 10484Thioacetic acidHCID 11776TriphenylphosphineHCID 288726trans-2-(4-Hydroxycyclohexyl)-isoindole-1,3-dioneHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 59226264HCID 59226264, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of PPh3 (1.28 g, 4.9 mmol) in THF (12 mL) was added dropwise DEAD (852 mg, 4.9 mmol) at −10° C. After the white solid was appeared, compound 2-(4-hydroxycyclohexyl)isoindoline-1,3-dione (600 mg, 2.45 mmol) was added, followed by CH3COSH (0.35 mL, 4.9 mmol) at −10° C. The mixture was stirred at room temperature overnight. TLC (PE:EA=1:1) showed the reaction was complete. The mixture was poured into water (200 mL) and extracted with EtOAc (100 mL). The aqueous layer was extracted with EtOAc (100 mL×3). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo to give S-(4-(1,3-dioxoisoindolin-2-yl)cyclohexyl) ethanethioate (600 mg, 81%) as a white solid.

Workup

  1. extractionextracted with EtOAc (100 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (100 mL×3)
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-74d86e92681744a2aa16074d63ea815e
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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