p-Toluenesulfonic acid → HCID 9909641, compound

HRID 1265166Notes

Reaction equation

HRID 1265166 reaction equation
[F:1][C:2]1[C:3]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=2[CH3:21])=[C:4]([CH:9]=[CH:10][C:11]=1[F:12])[C:5]([NH:7][NH2:8])=[O:6].[CH:22](OCC)(OCC)OCC.CC1C=CC(S(O)(=O)=O)=CC=1>CCO>[F:1][C:2]1[C:11]([F:12])=[CH:10][CH:9]=[C:4]([C:5]2[O:6][CH:22]=[N:8][N:7]=2)[C:3]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=1[CH3:21]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 12045116HCID 12045116, compound

Product 1

HCID 9909641HCID 9909641, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,4-Difluoro-2-(4-iodo-2-methyl-phenylamino)-benzoic acid hydrazide (146 mg, 0.36 mmol) was suspended in 7 mL of absolute EtOH and 2 mL of HC(OEt)3 was added along with approximately 3 mg of pTsOH> The reaction was heated to reflux for 3 h, cooled and concentration on a rotary evaporator. The reaction was purified (SiO2, 4:1 Hexane/EtOAc) to afford 117 mg (79%) of (2,3-difluoro-6-[1,3,4]oxadiazol-2-yl-phenyl)-(4-iodo-2-methyl-phenyl)-amine as a yellow powder. M.p. =144.4-145.5° C. 1H NMR (400 MHz, CDCl3) δ8.89 (s, 1H), 8.44 (s, 1H), 7.66 (m, 1H), 7.52 (d, J=1.7 Hz, 1H), 7.38 (dd, J=8.5, 1.9 Hz, 1 H), 6.83 (m, 1H), 6.14 (dd, J=8.5, 5.9 Hz, 1 H), 2.37 (s, 3 H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. temperaturecooled
  4. concentrationconcentration
  5. customon a rotary evaporator
  6. customThe reaction was purified (SiO2, 4:1 Hexane/EtOAc)

Sources & evidence

ORD record
ord-b35c9a23e98e404cb5a833e1bc5cbd41
Source dataset
uspto-grants-2003_04
Patent number
US06545030B1

Reaction notes

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