1,2-Dichloroethane → N-(4-hydroxy-3-methylphenyl)-3-(trifluoromethyl)benzamide

HRID 1361616Notes

Reaction equation

HRID 1361616 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([CH3:22])[CH:16]=1.C(Cl)CCl>C(Cl)Cl>[OH:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([C:2]([F:1])([F:13])[F:12])[CH:4]=2)=[CH:16][C:17]=1[CH3:22]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 99633-(Trifluoromethyl)benzoic acidHCID 760815-Amino-2-hydroxytoluene

Product 1

HCID 58396799N-(4-hydroxy-3-methylphenyl)-3-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-(trifluoromethyl)benzoic acid (380 mg, 2.00 mmol), 4-amino-2-methylphenol (271 mg, 2.20 mmol) and EDC (767 mg, 4.00 mmol) was added CH2Cl2 (80 mL). The resulting mixture was stirred for 66 hours at RT, concentrated, dissolved in EtOAc and washed with water. The organics were dried over sodium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography (0-50% EtOAc/hexanes) to yield N-(4-hydroxy-3-methylphenyl)-3-(trifluoromethyl)benzamide as a white solid. MS m/z=296 [M+1]+. Calc'd for C15H12F3NO2: 295.26.

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in EtOAc
  3. washwashed with water
  4. dry with materialThe organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by silica gel chromatography (0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-acaad072cce24899bb24ba4761acbef7
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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