Triphosgene → HCID 789488, compound

HRID 1270373Notes

Reaction equation

HRID 1270373 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.Cl[C:16](Cl)([O:18]C(=O)OC(Cl)(Cl)Cl)Cl>CC#N>[C:9]1([N:8]2[C:3]3=[N:4][CH:5]=[CH:6][CH:7]=[C:2]3[NH:1][C:16]2=[O:18])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 106790912-N-phenylpyridine-2,3-diamine

Product 1

HCID 789488HCID 789488, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of 3-amino-N-phenylpyridin-2-amine from Step B (258 mg, 1.39 mmol) in CH3CN (15 mL) was added triphosgene (413 mg, 1.39 mmol) and the reaction mixture was stirred for 10 min at ambient temperature. The mixture was concentrated in vacuo and the crude solid was quenched with H2O (10 mL) and saturated aqueous NaHCO3 (10 mL). The precipitate was filtered, washed with water and air-dried to yield the title compound as a brown solid, which was of sufficient purity for use in the next step. MS: m/z=212 (M+1).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe crude solid was quenched with H2O (10 mL) and saturated aqueous NaHCO3 (10 mL)
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customair-dried

Sources & evidence

ORD record
ord-c8c5f8dbf7a343129eedc1d2ce5ef689
Source dataset
uspto-grants-2007_04
Patent number
US07202251B2

Reaction notes

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