4-Fluorobenzene-1,2-diamine → HCID 22139853, compound

HRID 2358187Notes

Reaction equation

HRID 2358187 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH2:9])[CH:3]=1.[Cl:10][C:11]1[C:12]([N:16]=[C:17]=[S:18])=[CH:13][S:14][CH:15]=1>C1COCC1>[NH2:9][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][C:5]=1[NH:8][C:17]([NH:16][C:12]1[C:11]([Cl:10])=[CH:15][S:14][CH:13]=1)=[S:18]

Participants

4

Reactant 2

HCID 1645844-Fluorobenzene-1,2-diamineHCID 22139828HCID 22139828, compound

Product 1

HCID 22139853HCID 22139853, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Fluoro-1,2-phenylendiamine (900 mg) was dissolved in THF (25 ml) and 4-chloro-3-thienylisothiocyanat (example 52c), dissolved in THF (15 ml), was added with stirring. The solution was stirred for about 3 h at room temperature and stood overnight. Then the reaction mixture was concentrated and the residue purified by preparative HPLC. The product containing fractions were combined, the acetonitrile was removed, the aqueous residue made basic and three times extracted with ethyl acetate. The organic layers were combined, dried (MgSO4) and filtered. After removal of the solvent the desired product (625 mg) was obtained.

Workup

  1. additionwas added
  2. stirringThe solution was stirred for about 3 h at room temperature
  3. concentrationThen the reaction mixture was concentrated
  4. customthe residue purified by preparative HPLC
  5. additionThe product containing fractions
  6. customthe acetonitrile was removed
  7. extractionthree times extracted with ethyl acetate
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customAfter removal of the solvent the desired product (625 mg)
  11. customwas obtained

Sources & evidence

ORD record
ord-f3a9642735ee4a279b1d5762ef1fce11
Source dataset
uspto-grants-2010_07
Patent number
US07763643B2

Reaction notes

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