Triethylamine → HCID 59381915, compound

HRID 453366Notes

Reaction equation

HRID 453366 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].C(N(CC)CC)C.[NH2:22][C:23]1[CH:24]=[CH:25][C:26]([CH3:32])=[C:27]([CH:31]=1)[C:28]([OH:30])=[O:29]>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4]([NH:22][C:23]1[CH:24]=[CH:25][C:26]([CH3:32])=[C:27]([CH:31]=1)[C:28]([OH:30])=[O:29])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27348802-Fluoro-5-(trifluoromethyl)benzoyl ChlorideHCID 103746145-Amino-2-methylbenzoic acid

Product 1

HCID 59381915HCID 59381915, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 100 mL round-bottomed flask containing 2-fluoro-5-(trifluoromethyl)benzoyl chloride (0.44 ml, 2.9 mmol) in CH2Cl2 (30 mL) was added triethylamine (0.48 ml, 3.4 mmol). After 10 min, 5-amino-2-methylbenzoic acid (0.400 g, 2.6 mmol) was added. The solution was stirred at rt overnight. After cooling, the crude reaction mixture was concentrated to remove excess NEt3 then diluted with CH2Cl2 and washed with 1 N HCl once, and brine & salt once then dried over Na2SO4 to afford 5-(2-fluoro-5-(trifluoromethyl)benzamido)-2-methylbenzoic acid 32 as an off-white solid. MS m/z found: 342.1 (ESI, pos. ion).

Workup

  1. temperatureAfter cooling
  2. customthe crude reaction mixture
  3. concentrationwas concentrated
  4. customto remove excess NEt3
  5. additionthen diluted with CH2Cl2
  6. washwashed with 1 N HCl once
  7. dry with materialbrine & salt once then dried over Na2SO4

Sources & evidence

ORD record
ord-87ba79a698ee435da9fc5d4ff926dc3f
Source dataset
uspto-grants-2013_07
Patent number
US08492404B2

Reaction notes

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