Hydrochloric Acid → HCID 178419066, compound

HRID 1846764Notes

Reaction equation

HRID 1846764 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[NH2:9].CCO[C:13]([S-:15])=[S:14].[K+].Cl>CN(C=O)C>[F:8][C:5]1[CH:6]=[CH:7][C:2]2[S:14][C:13]([SH:15])=[N:9][C:3]=2[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 677752,5-DifluoroanilineHCID 2735045Potassium ethylxanthate

Product 1

HCID 178419066HCID 178419066, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2,5-difluoro-phenylamine (129 mg, 1 mmol) and potassium o-ethyl dithiocarbonate (352 mg, 2.2 mmol) in DMF (5 mL) was heated to 120° C. for 15 min in microwave. The reaction mixture was cooled, diluted with 10 mL of ice water, and acidified with 3 mL of HCl solution (1 mol/L). Then the mixture was extracted with EtOAc (3×50 mL), washed with brine and dried over Na2SO4. The dried organic layers were concentrated to give 5-fluorobenzo[d]thiazole-2-thiol (120 mg, 0.67 mmol, 67%). ESI-MS (M+1): 185 calc. for C7H4FN4S2 184.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThen the mixture was extracted with EtOAc (3×50 mL)
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationThe dried organic layers were concentrated

Sources & evidence

ORD record
ord-12e26a863ec145908fe04a17fb31f3d1
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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