Dimethylformamide → HCID 22258081, compound

HRID 1610999Notes

Reaction equation

HRID 1610999 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[C:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])=[CH:14][CH:13]=[CH:12][C:11]=1[CH:25](O)[C:26]([OH:28])=[O:27].[S:30](Cl)(Cl)=O.CN(C=O)C.S1C=CC=C1CC(O)=O.CC(C)([O-])C.[K+]>C(Cl)Cl.CCO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[C:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])=[CH:14][CH:13]=[CH:12][C:11]=1[CH:25]([SH:30])[C:26]([OH:28])=[O:27]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 159702-Thiopheneacetic acidHCID 24386Thionyl ChlorideHCID 9932554HCID 9932554, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22258081HCID 22258081, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Example 1 Part B compound (462 mg, 1.00 mmol) in CH2Cl2 (5 mL) under argon at room temperature was added thionyl chloride (80 μL, 1.1 mmol) and then DMF (80 μL, 1.0 mmol) over 2 min. The reaction mixture was stirred for 1 h, then quenched with saturated sodium bicarbonate solution and extracted twice with CH2Cl2. The extracts were combined, dried (MgSO4) and evaporated. The residuum was immediately dissolved in EtOH (5 mL) and added to a solution prepared from thiolacetic acid (0.35 mL, 4.9 mmol) and potassium t-butoxide (539 mg, 4.8 mmol) in EtOH (5 mL). After 16 h, the reaction mixture was quenched with water and extracted three times with EtOAc. The organic extracts were combined, dried (MgSO4) and evaporated. Purification by flash chromatography on silica gel provided the title compound as a colorless oil, 330 mg (64% yield). LC/MS gave the correct molecular ion [(M+H)+=519] for the desired compound.

Workup

  1. customquenched with saturated sodium bicarbonate solution
  2. extractionextracted twice with CH2Cl2
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. dissolutionThe residuum was immediately dissolved in EtOH (5 mL)
  6. additionadded to a solution
  7. waitAfter 16 h
  8. customthe reaction mixture was quenched with water
  9. extractionextracted three times with EtOAc
  10. dry with materialdried (MgSO4)
  11. customevaporated
  12. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-764d41564eec4c1091799454cf997566
Source dataset
uspto-grants-2006_01
Patent number
US06984645B2

Reaction notes

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