O-Phenylenediamine → HCID 59351261, compound

HRID 887405Notes

Reaction equation

HRID 887405 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]=[C:16]=S)=[CH:11][CH:10]=2)=[N:6][CH:5]=[CH:4][N:3]=1.[C:18]1([NH2:25])[C:19]([NH2:24])=[CH:20][CH:21]=[CH:22][CH:23]=1.C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1.C(Cl)Cl>[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[NH:25][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[N:24]=3)=[CH:11][CH:10]=2)=[N:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 7243O-PhenylenediamineHCID 10868DicyclohexylcarbodiimideHCID 59351155HCID 59351155, compound

Product 1

HCID 59351261HCID 59351261, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

The mixture of 2-chloro-3-(4-isothiocyanatophenoxy)pyrazine (190 mg, 721 mmol), benzene-1,2-diamine (93.5 mg, 865 μmol) and N,N′-dicyclohexylcarbodiimide (223 mg, 1081 μmol) in THF (1.5 ml) was heated at 75° C. for 1.5 hrs. The mixture was cooled to room temperature, diluted with DCM and absorbed onto silica for purification using a 20-100% EtOAc/hexanes gradient to give the desired product.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customabsorbed onto silica for purification

Sources & evidence

ORD record
ord-7e962b29519a4ccdb1f74b9b73e22008
Source dataset
uspto-grants-2012_08
Patent number
US08247418B2

Reaction notes

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