Thiophosgene → 4-(2-Chloro-5-isothiocyanatophenyl)-3-fluoropyridine

HRID 30801Notes

Reaction equation

HRID 30801 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[F:15].C(=O)(O)[O-].[Na+].[C:21](Cl)(Cl)=[S:22]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:21]=[S:22])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[F:15]

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 690046574-Chloro-3-(3-fluoropyridin-4-yl)benzenamine

Product 1

HCID 860453294-(2-Chloro-5-isothiocyanatophenyl)-3-fluoropyridine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

The mixture containing 4-chloro-3-(3-fluoropyridin-4-yl)benzenamine (1 eq) and sodium bicarbonate (2 eq) in acetone was treated with thiophosgene (2 eq) and stirred for 5 minutes at 0° C. Reaction then concentrated and partitioned between ethyl acetate and water. Organic layer dried over sodium sulfate and sodium bicarbonate and concentrated to give 4-(2-chloro-5-isothiocyanatophenyl)-3-fluoropyridine. HPLC=5.54 min; MS: MH+=265.

Workup

  1. customReaction
  2. concentrationthen concentrated
  3. custompartitioned between ethyl acetate and water
  4. dry with materialOrganic layer dried over sodium sulfate and sodium bicarbonate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-268b0d3cd39b4da6b661c20374790de7
Source dataset
uspto-grants-2008_09
Patent number
US07423150B2

Reaction notes

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