Phosgene → 4-(2-(4-Isocyanato-2-methylphenoxy)pyridin-3-yl)pyrimidine

HRID 1361674Notes

Reaction equation

HRID 1361674 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:21])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][N:16]=2)=[CH:13][CH:12]=[CH:11][N:10]=1.[C:22](=O)(O)[O-:23].[Na+].C(Cl)(Cl)=O>C(Cl)Cl>[N:21]([C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][N:16]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)=[C:2]([CH3:1])[CH:3]=1)=[C:22]=[O:23]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 516892Sodium BicarbonateHCID 583971983-Methyl-4-(3-(pyrimidin-4-yl)pyridin-2-yloxy)benzenamine

Product 1

HCID 866025954-(2-(4-Isocyanato-2-methylphenoxy)pyridin-3-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 3-methyl-4-(3-(pyrimidin-4-yl)pyridin-2-yloxy)benzenamine (93 mg, 0.33 mmol) in CH2Cl2 (8 mL) was added saturated sodium bicarbonate (4 mL) followed 5 minutes later by phosgene (20% solution in toluene, 0.27 mL, 0.50 mmol). The mixture was stirred for 15 minutes at RT, diluted with CH2Cl2 and extracted with water. The organic layer was dried over sodium sulfate, filtered, concentrated and used without purification.

Workup

  1. extractionextracted with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customused without purification

Sources & evidence

ORD record
ord-abe92689dbbb4747beb3b749a7ed4c8e
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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