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

HRID 446268Notes

Reaction equation

HRID 446268 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-b4fdd4f8fbae45cc95ca199ee177dbc2
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Reaction notes

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