Dimethylformamide → HCID 70220324, compound

HRID 568211Notes

Reaction equation

HRID 568211 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].C(N(CC)CC)C.C[N:18]([CH:20]=[O:21])C.C(Cl)(=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:20]([NH2:18])=[O:21])=[C:3]([CH3:9])[CH:4]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 178194-Amino-m-cresol

Product 1

HCID 70220324HCID 70220324, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Amino-3-methylphenol (370 mg, 3.00 mmols) was put into a 30-ml conical flask, purged with argon, and dissolved in 1.3 ml of dry DMF. Next, 0.42 ml (1 eq.) of dry triethylamine was added. Then, a dry DMF solution (3.0 ml) of benzoyl chloride (0.35 ml) was added, and stirred at room temperature for 12 hours. The resulting reaction mixture was poured into 50 ml of cold water, suction filtered, extracted with methylene chloride, and washed with water. The methylene chloride layer was dried with sodium sulfate, and methylene chloride was removed by evaporation under reduced pressure. Next, the residue was purified by column clromnatography (silica gel eluted with methylene chloride) to obtain 400 mg of the intended product, 4-hydroxy-2-methylphenylbenzamide (yield: 60%).

Workup

  1. custompurged with argon
  2. dissolutiondissolved in 1.3 ml of dry DMF
  3. customThe resulting reaction mixture
  4. filtrationfiltered
  5. extractionextracted with methylene chloride
  6. washwashed with water
  7. dry with materialThe methylene chloride layer was dried with sodium sulfate, and methylene chloride
  8. customwas removed by evaporation under reduced pressure
  9. customNext, the residue was purified by column clromnatography (silica gel eluted with methylene chloride)

Sources & evidence

ORD record
ord-f575f9ab5cf646ac802a852f9ee24c14
Source dataset
uspto-grants-2001_01
Patent number
US06180844B2

Reaction notes

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