Trifluoroacetic acid methylene chloride → Trifluoroacetate

HRID 1671363Notes

Reaction equation

HRID 1671363 reaction equation
[F:1][CH:2]([F:28])[S:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:27])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19]C(=O)OC(C)(C)C)=[CH:15][CH:14]=2)=[CH:6][CH:5]=1.[F:29][C:30]([F:35])([F:34])[C:31]([OH:33])=[O:32].ClCCl>ClCCCl>[F:29][C:30]([F:35])([F:34])[C:31]([O-:33])=[O:32].[F:29][C:30]([F:35])([F:34])[C:31]([OH:33])=[O:32].[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][C:11]([NH:10][C:7]2[CH:8]=[CH:9][C:4]([S:3][CH:2]([F:28])[F:1])=[CH:5][CH:6]=2)=[O:27])=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 35022671HCID 35022671, compound

Product 2

HCID 84468TrifluoroacetateHCID 67348104HCID 67348104, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Tert-butyl 4-[2-({4-[(difluoromethyl)thio]phenyl}amino)-2-oxoethyl]phenylcarbamate (Example 27) (3.63 g) was stirred in 25% trifluoroacetic acid/dichloromethane at room temperature for 45 minutes. The mixture was diluted with 1,2-dichloroethane (25 mL) and evaporated down twice. The residue was recrystallized from ethyl acetate (15 mL) and hexane (15 mL). The product was obtained as the 1:1 trifluoroacetate salt, 2-(4-aminophenyl)-N-(4-(difluoromethylthio)phenyl)acetamide 2,2,2-trifluoroacetate: 1H NMR (300 MHz, DMSO-d6) δ ppm 3.45-4.13 (m, 2H) 3.62 (s, 2H) 7.03 (d, J=8.5 Hz, 2H) 7.38 (t, J=56.1 Hz, 1H) 7.28 (d, J=8.5 Hz, 2H) 7.47-7.55 (m, 2H) 7.64-7.72 (m, 2H) 10.36 (s, 1H) MS (DCI/NH3) m/z 309.0 (M+H)+; Anal. C15H14F2N2OS C2HF3O2: C, H, N.

Workup

  1. customevaporated down twice
  2. customThe residue was recrystallized from ethyl acetate (15 mL) and hexane (15 mL)

Sources & evidence

ORD record
ord-c21ba11755c34f669e6d2a6d3c6842a0
Source dataset
uspto-grants-2011_08
Patent number
US07994223B2

Reaction notes

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