Dimethylformamide → HCID 15614937, compound

HRID 620355Notes

Reaction equation

HRID 620355 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:16][CH3:17])[C:8]=2[C:12]([F:15])([F:14])[F:13])[C:3]=1[C:18]([OH:20])=O.S(Cl)(Cl)=O.C[N:26](C)C=O>>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:16][CH3:17])[C:8]=2[C:12]([F:15])([F:14])[F:13])[C:3]=1[C:18]([NH2:26])=[O:20]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 15614957HCID 15614957, compound

Product 1

HCID 15614937HCID 15614937, compound

Conditions

Temperature
60 °C

Procedure

A suspension of 2-bromo-6-methoxy-5-trifluoromethyl-1-naphthoic acid (2.0 g, 5.73 mmol, prepared by the process of Example 11, Step 2), thionyl chloride (11 mL) and dimethylformamide (40 μl, 0.095 eq) was heated with stirring at 60° C. under a dry N2 atmosphere for 35 minutes. The reaction mixture was cooled to room temperature and the thionyl chloride was removed. The solid residue was dissolved in THF (20 mL) and this solution was added dropwise to stirred, cold (0°-5° C.) ammonium hydroxide over a 5 minute period. After 15 minutes water (100 mL) was added and the suspension was filtered. The solid was washed with water and dried in vacuo to yield the title compound as a white solid in (1.80 g, 90%)

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe thionyl chloride was removed
  4. dissolutionThe solid residue was dissolved in THF (20 mL)
  5. additionthis solution was added dropwise
  6. stirringto stirred
  7. waitcold (0°-5° C.) ammonium hydroxide over a 5 minute period
  8. additionAfter 15 minutes water (100 mL) was added
  9. filtrationthe suspension was filtered
  10. washThe solid was washed with water
  11. customdried in vacuo

Sources & evidence

ORD record
ord-040d0e1427864426b8bb2520bfeb9565
Source dataset
uspto-grants-1989_04
Patent number
US04820727

Reaction notes

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