O-Phenylenediamine → HCID 46208939, compound

HRID 555818Notes

Reaction equation

HRID 555818 reaction equation
Cl[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:33]=[N:34][CH:35]2[CH2:40]CCCC2)CCCCC1.C1C[O:44][CH2:43]C1>C(Cl)Cl>[O:44]1[CH2:43][CH2:33][N:34]([C:2]2[C:7]([O:8][C:9]3[CH:14]=[CH:13][C:12]([NH:15][C:16]4[NH:25][C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=5[N:24]=4)=[CH:11][CH:10]=3)=[N:6][CH:5]=[CH:4][N:3]=2)[CH2:35][CH2:40]1

Participants

6

Reactant 4

HCID 7243O-PhenylenediamineHCID 8028TetrahydrofuranHCID 10868DicyclohexylcarbodiimideHCID 59351155HCID 59351155, compound

Product 1

HCID 46208939HCID 46208939, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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-8bbd101189f044efbf5c344e5df0b1cc
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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