Dimethylformamide → HCID 178454934, compound

HRID 1817916Notes

Reaction equation

HRID 1817916 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][C:5]=1CC(C)(C)C(N)=O.O1[C:24]2([CH2:29]COC[CH2:25]2)[CH2:23]1.[P].[S].C[N:33]([CH3:36])C=O>O>[C:24]([C:36]1[NH:3][C:4]2[CH:9]=[CH:8][C:7]([S:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[CH:6][C:5]=2[N:33]=1)([CH3:29])([CH3:25])[CH3:23]

Participants

8

Reactant 6

HCID 6228Dimethylformamide3×HCID 24758Sodium hydrideHCID 1604391,6-Dioxaspiro[2.5]octaneHCID 5362487SulfurHCID 5462309PhosphorusHCID 86604772HCID 86604772, compound

Product 1

HCID 178454934HCID 178454934, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of sodium hydride (34 mg, 0.86 mmol) in N,N-dimethylformamide (1 mL) was added a N,N-dimethylformamide solution of N-[2-amino-5-(tert-butylthio)pheny]-2,2-dimethylpropanamide (Step C, 200 mg, 0.71 mmol) at room temperature. After stirring for 30 min, a N,N-dimethylformamide solution of 1,6-dioxaspiro[2,5]octane (Phosphorus and Sulfur and the Related Elements 1984, 19, 113-129., 98 mg, 0.86 mmol) was added. The mixture was stirred at room temperature for 3 h and at 100° C. for 5 h. Water (10 mL) was added and the mixture was extracted with ethyl acetate (15 mL). The organic extract was washed with water (5 mL) and brine (5 mL) and concentrated. The residue was purified by pTLC (ethyl acetate:hexane=1:2 as eluent) to afford the title compound as pale brown oil.

Workup

  1. addition, 98 mg, 0.86 mmol) was added
  2. stirringThe mixture was stirred at room temperature for 3 h and at 100° C. for 5 h
  3. extractionthe mixture was extracted with ethyl acetate (15 mL)
  4. extractionThe organic extract
  5. washwas washed with water (5 mL) and brine (5 mL)
  6. concentrationconcentrated
  7. customThe residue was purified by pTLC (ethyl acetate:hexane=1:2 as eluent)

Sources & evidence

ORD record
ord-e9cfab67afbf41efb353714387efde64
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Reaction notes

Loading…