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

HRID 2040955Notes

Reaction equation

HRID 2040955 reaction equation
F[C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].CCO[C:13]([S-:15])=[S:14].[K+]>CN(C)C=O.O.Cl>[I:9][C:7]1[CH:6]=[CH:5][C:3]2[N:4]=[C:13]([SH:15])[S:14][C:2]=2[CH:8]=1

Participants

6

Reactant 2

HCID 1856942-Fluoro-4-iodoanilineHCID 2735045Potassium ethylxanthate

Product 1

HCID 178527793HCID 178527793, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 2-fluoro-4-iodoaniline (24.19 g, 0.100 mole) and potassium ethylxanthogenate (35.27 g, 0.220 mole) in N,N-dimethylformamide (80 mL) was stirred at 95° C. for 5 hours. The reaction mixture was cooled to room temperature then diluted with water (150 mL) and 1 N aqueous HCl (200 mL). The mixture was stirred at room temperature overnight. The resulting precipitate was collected by filtration and rinsed with water. The solid was dried overnight at 85° C. in a vacuum oven to provide 6-iodobenzo[d]thiazole-2-thiol. 1H NMR (300 MHz, CD3OD) δ ppm 7.09 (d, J=8 Hz, 1H), 7.70 (dd, J=2, 8 Hz, 1H), 8.10 (d, J=2 Hz, 1H), 13.82 (sbroad, 1H); MS (DCI/NH3) m/z 294 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringThe mixture was stirred at room temperature overnight
  3. filtrationThe resulting precipitate was collected by filtration
  4. washrinsed with water
  5. customThe solid was dried overnight at 85° C. in a vacuum oven

Sources & evidence

ORD record
ord-3c02e6c572b04873b037e44fd9a27e00
Source dataset
uspto-grants-2013_11
Patent number
US08580968B2

Reaction notes

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