Hydrochloric Acid → HCID 10115851, compound

HRID 2218462Notes

Reaction equation

HRID 2218462 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:23]([F:24])=[C:22]([F:25])[C:21]([F:26])=[CH:20][C:10]=2[C:11]([NH:13][O:14][CH2:15][CH2:16][O:17]C=C)=[O:12])=[C:4]([CH3:27])[CH:3]=1.Cl.O>C(O)C>[OH:17][CH2:16][CH2:15][O:14][NH:13][C:11](=[O:12])[C:10]1[CH:20]=[C:21]([F:26])[C:22]([F:25])=[C:23]([F:24])[C:9]=1[NH:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][C:4]=1[CH3:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 22286309HCID 22286309, compound

Product 1

HCID 10115851HCID 10115851, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(4-iodo-2-methyl-phenylamino)-3,4,5-trifluoro-N-(2-vinyloxyethoxy)-benzamide (3.00 g, 6.09 mmol) in ethanol (80 mL) was treated with 1 M aqueous hydrochloric acid (16 mL, 16 mol). The resultant solution was stirred for 2.5 h at ambient temperature. Water (50 mL) was added and the slurry was filtered. The solids were washed with ethanol-water (1:1, 150 mL) and recrystallized from methanol-acetone to afford N-(2-hydroxyethoxy)-2-(4-iodo-2-methyl-phenylamino)-3,4,5-trifluoro-benzamide (2.12 g, 75%): m.p. 205-207° C. (dec); 1H NMR (400 MHz, DMSO-d6) δ 11.85 (br s, 1 H), 8.13 (s, 1 H), 7.54 (dd, J=8.9, 8.7 Hz, 1 H), 7.47 (d, J=1.0 Hz, 1 H), 7.32 9d, J=8.5 Hz, 1 H), 6.41 (dd, J=8.1, 5.0 Hz, 1 H), 4.69 (br s, 1 H), 3.79 (br s, 2 H), 3.52 (br s, 2 H), 2.20 (s, 3 H); MS (APCI+)=467.1; MS (APCI−)=465.1; Anal. Calcd/found for C16H14F3IN2O3: C, 41.22/41.28; H, 3.03/2.91; N, 6.01/5.79.

Workup

  1. filtrationthe slurry was filtered
  2. washThe solids were washed with ethanol-water (1:1, 150 mL)
  3. customrecrystallized from methanol-acetone

Sources & evidence

ORD record
ord-00df981e8e8646a38256e56354245c77
Source dataset
uspto-grants-2008_08
Patent number
US07411001B2

Reaction notes

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