Dimethylformamide → HCID 70216367, compound

HRID 568210Notes

Reaction equation

HRID 568210 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:22]1([C:28]2[CH:36]=[CH:35][C:31](C(Cl)=O)=[CH:30][CH:29]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([C:26]2[CH:27]=[C:22]([C:28]3[CH:36]=[CH:35][CH:31]=[CH:30][CH:29]=3)[CH:23]=[CH:24][C:25]=2[C:20]([NH2:18])=[O:21])=[C:3]([CH3:9])[CH:4]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 178194-Amino-m-cresolHCID 841514-Phenylbenzoyl chloride

Product 1

HCID 70216367HCID 70216367, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Amino-3-methylphenol (270 mg, 2.20 mmols) was put into a 30-ml conical flask, purged with argon, and dissolved in 1.0 ml of dry DMF. Next, 0.3 ml (1 eq.) of dry triethylamine was added. Next, a dry DMF solution (3.0 ml) of 4-phenylbenzoyl chloride (478 mg) was added, and stirred at room temperature for 12 hours. The resulting reaction mixture was poured into 100 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 chromatography (silica gel eluted with methylene chloride) to obtain 648 mg of the intended product, 4-hydroxy-2-methylphenyl-4-phenylbenzamide (yield: 96%).

Workup

  1. custompurged with argon
  2. dissolutiondissolved in 1.0 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 chromatography (silica gel eluted with methylene chloride)

Sources & evidence

ORD record
ord-836917eb492f4352a1a400ec74a7ab9b
Source dataset
uspto-grants-2001_01
Patent number
US06180844B2

Reaction notes

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