Dimethylformamide → HCID 4186278, compound

HRID 2389261Notes

Reaction equation

HRID 2389261 reaction equation
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[CH:16]3)=[CH:9][CH:8]=1.[OH-].[Na+].CN(C)[CH:26]=[O:27]>>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[C:16]3[CH:26]=[O:27])=[CH:11][CH:12]=1

Participants

5

Reactant 4

HCID 6228Dimethylformamide3×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 59145396HCID 59145396, compound

Product 1

HCID 4186278HCID 4186278, compound

Procedure

In a 100-ml round-bottom flask is placed 2.8 mL of dimethylformamide (2.74 g, 3.74 mmol). The flask and the content was cooled in an ice-salt bath for about 0.5 hour and 0.86 mL (1.44 g, 94 mmol) of freshly distilled phosphorusoxychloride is subsequently added with stirring to the dimethylformamide dropwise. Then a solution of 1.0 g of 32 (85 mmol) in 1 mL of dimethylformamide is added to the above solution slowly. After the addition, the temperature of the solution is brought to 40° C. and allowed to stir for an hour. At this time, 1N NaOH (10 mL) was added to the reaction mixture dropwise. The resulting mixture is heated rapidly to the boiling point and allowed to cool to room temperature. The resulting precipitate is collected on a filter and the solid was further washed with water. Compound 33 obtained from this procedure was pure enough for the next reaction. MS (Es+ve) m/z 300, (Es−ve) m/z 298.

Workup

  1. customIn a 100-ml round-bottom flask is placed
  2. temperatureThe flask and the content was cooled in an ice-salt bath for about 0.5 hour
  3. additionAfter the addition
  4. customis brought to 40° C.
  5. temperatureThe resulting mixture is heated rapidly to the boiling point
  6. customThe resulting precipitate is collected on
  7. filtrationa filter
  8. washthe solid was further washed with water

Sources & evidence

ORD record
ord-17fd92fa94e445af9602791e49a28eea
Source dataset
uspto-grants-2012_09
Patent number
US08273744B2

Reaction notes

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