Acetic Acid → HCID 10481464, compound

HRID 915264Notes

Reaction equation

HRID 915264 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[S:11][CH:12]=[C:13]([C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)=[O:16])[N:14]=1.C(O)(=O)C.[Br:32]Br>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[S:11][C:12]([Br:32])=[C:13]([C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:26])([F:27])[F:25])=[CH:20][CH:19]=2)=[O:16])[N:14]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 11661966HCID 11661966, compound

Product 1

HCID 10481464HCID 10481464, compound

Procedure

To a 50-mL flask was added {2-[(2,6-dichlorophenyl)amino](1,3-thiazol-4-yl)}-N-[4-(trifluoromethyl)phenyl]-carboxamide, Example 63, (100 mg, 0.23 mmol), acetic acid (2.0 mL), and bromine (0.03 mL, 0.46 mmol, Aldrich). The reaction mixture was stirred at room temperature overnight, then concentrated in vacuo. The crude product was diluted with CH2Cl2 (50 mL), washed with satd NaHCO3 (2×), 1 M Na2S2O3 and brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (12% EtOAc in hexane) provided the title product as an off-white solid. MS (ESI, pos. ion) m/z: 512 (M+1). MP: 151-162° C.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe crude product was diluted with CH2Cl2 (50 mL)
  3. washwashed with satd NaHCO3 (2×), 1 M Na2S2O3 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by silica gel chromatography (12% EtOAc in hexane)

Sources & evidence

ORD record
ord-a19a63dd9115473aaff3e5a45c49a599
Source dataset
uspto-grants-2007_09
Patent number
US07265138B2

Reaction notes

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