2,4-Dichloro-1-isothiocyanatobenzene → Ethyl 3-[(2-amino-6-{[(2,4-dichlorophenyl)carbamothioyl]amino}phenyl)amino]-2,2-difluoropropanoate

HRID 1628520Notes

Reaction equation

HRID 1628520 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[C:3]=1[NH:9][CH2:10][C:11]([F:18])([F:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13].[Cl:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=1[N:27]=[C:28]=[S:29]>O1CCCC1>[NH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:28](=[S:29])[NH:27][C:21]2[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:20]=2[Cl:19])[C:3]=1[NH:9][CH2:10][C:11]([F:17])([F:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 810662,4-Dichloro-1-isothiocyanatobenzeneHCID 68739019Ethyl 3-[(2,6-diaminophenyl)amino]-2,2-difluoropropanoate

Product 1

HCID 86632899Ethyl 3-[(2-amino-6-{[(2,4-dichlorophenyl)carbamothioyl]amino}phenyl)amino]-2,2-difluoropropanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-[(2,6-diaminophenyl)amino]-2,2-difluoropropanoate (998.3 mg, 3.851 mmol) in tetrahydrofuran (20 mL) was added a solution of 2,4-dichlorophenyl isothiocyanate (785.9 mg, 3.851 mmol) at 0° C. The resultant mixture was stirred at 0° C. for 1 hr and warmed to room temperature and stirred for 2 hrs. After removal of solvent, the residue was purified by silica gel column chromatography eluting with a 0-60% ethyl acetate/n-hexane gradient mixture to give the title compound as an amorphous (1.61 g, 3.486 mmol, 91%).

Workup

  1. customAfter removal of solvent
  2. customthe residue was purified by silica gel column chromatography
  3. washeluting with a 0-60% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-eee44210a7b7493182df2514d82cd3ca
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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