Hydrochloric Acid → 7-Fluoro-1,3-benzothiazol-2-amine

HRID 2202366Notes

Reaction equation

HRID 2202366 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[S:11][C:12]#[N:13].C(O)C.Cl>O>[F:1][C:2]1[C:3]2[S:11][C:12]([NH2:13])=[N:8][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 904190222-Fluoro-6-nitrophenylthiocyanate

Product 1

HCID 148922457-Fluoro-1,3-benzothiazol-2-amineYield 29.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-fluoro-3-nitro-2-thiocyanatobenzene 2 (3.96 g, 0.02 mol), ethanol (30 mL), water (25 mL) and conc. hydrochloric acid (25 mL) was refluxed gently during the addition of hydrogen-reduced iron powder (8 g). After refluxing for 16 hr, the liquor was filtered hot, cooled, the residue filtered, dissolved in hot water, and neutralized with ammonia and then extracted with EtOAc to get the compound 7-fluorobenzo[d]thiazol-2-amine (1 g) as a colorless oil. LC-MS: m/z 169.2 (M+H)+

Workup

  1. temperatureAfter refluxing for 16 hr
  2. filtrationthe liquor was filtered hot
  3. temperaturecooled
  4. filtrationthe residue filtered
  5. dissolutiondissolved in hot water
  6. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-9ea32e9d4cb2489ea1c7a9824bd613c8
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

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