2-Fluoro-4-iodoaniline → HCID 178527793, compound

HRID 1848109Notes

Reaction equation

HRID 1848109 reaction equation
F[C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:10]([S-:15])(=[S:14])OCC.[Na+]>CN(C=O)C.O.Cl>[I:9][C:7]1[CH:6]=[CH:5][C:3]2[N:4]=[C:10]([SH:15])[S:14][C:2]=2[CH:8]=1

Participants

6

Reactant 2

HCID 1856942-Fluoro-4-iodoanilineHCID 23690437Sodium ethylxanthate

Product 1

HCID 178527793HCID 178527793, compoundYield 112.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 2-fluoro-4-iodoaniline (2.4 g, 10 mmol) and sodium O-ethyl carbonodithioate (3.2 g, 20 mmol) in DMF (8 mL) was stirred at 95° C. for 5 h. The reaction mixture was cooled to rt then diluted with water (25 mL) and 1 N aqueous HCl (20 mL). The mixture was stirred at room temperature for 1 h. The resulting precipitate was collected by filtration and washed with water. The solid was dried to afford 6-iodobenzo[d]thiazole-2-thiol as a light yellow solid (3.3 g, 100%). 1H NMR (300 MHz, CD3OD) δ 7.89 (d, J=1.2 Hz, 1H), 7.67 (dd, J=1.8, 8.7 Hz, 1H), 7.05 (d, J=8.4 Hz, 1H). LCMS (ESI) m/z 294 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. stirringThe mixture was stirred at room temperature for 1 h
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water
  5. customThe solid was dried

Sources & evidence

ORD record
ord-ac19c4c0b5f04b63935934547a840304
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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