Hydrochloric Acid → HCID 178427887, compound

HRID 1265167Notes

Reaction equation

HRID 1265167 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].[C:22](=S)=[S:23].[OH-].[K+].Cl>CCO.CCOC(C)=O.O>[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]([C:5]2[O:6][C:22]([SH:23])=[N:8][N:7]=2)[CH:9]=[CH:10][C:11]=1[F:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 12045116HCID 12045116, compound

Product 1

HCID 178427887HCID 178427887, compoundYield 51.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

3,4-Difluoro-2-(4-iodo-2-methyl-phenylamino)-benzoic acid hydrazide (170 mg, 0.42 mmol) was suspended in 7 mL of absolute EtOH and cooled to 0° C. Carbon disulfide (74 mg, 0.97 mmol) was added followed by 24 mg (0.42 mmol) of powdered KOH. The reaction was stirred for 1 h at 0° C., 1 h at rt, and refluxed for 3 h to afford a homogeneous reaction. The reaction was cooled to rt. at which point a ppt formed. Water was added and the reaction diluted with 5 mL of EtOAc. 1N HCl was added to acidify the aqueous layer (pH=2). The aqueous layer was extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4 and concentrated to obtain 96 mg (51%) of 5-[3,4-Difluoro-2-(4-iodo-2-methyl-phenylamino)-phenyl]-[1,3,4]oxadiazole-2-thiol as a yellow powder. M.p.=231.8-232.8° C. 1H NMR (400 MHz, CDCl3) δ7.62 (m, 2H), 7.47 (s, 1H), 7.30 (complex m, 2H), 6.44 (dd, J=8.0, 4.5 Hz, 1H), 2.19 (s, 3H).

Workup

  1. temperaturerefluxed for 3 h
  2. customto afford
  3. customa homogeneous reaction
  4. temperatureThe reaction was cooled to rt
  5. customat which point a ppt formed
  6. extractionThe aqueous layer was extracted with EtOAc (3×)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6f4d1fb99b6c4b6c88edf4c2ac1174dd
Source dataset
uspto-grants-2003_04
Patent number
US06545030B1

Reaction notes

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