Diphosgene → 5-chloro-3,4-dihydro-7-fluoro-2H-1-benzopyran-8-yl isocyanate

HRID 440689Notes

Reaction equation

HRID 440689 reaction equation
[NH2:1][C:2]1[C:11]2[O:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([Cl:12])=[CH:4][C:3]=1[F:13].Cl[C:15](OC(Cl)(Cl)Cl)=[O:16]>C1(C)C=CC=CC=1>[Cl:12][C:5]1[C:6]2[CH2:7][CH2:8][CH2:9][O:10][C:11]=2[C:2]([N:1]=[C:15]=[O:16])=[C:3]([F:13])[CH:4]=1

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 224047928-amino-5-chloro-3,4-dihydro-7-fluoro-2H-1-benzopyran

Product 1

HCID 224047285-chloro-3,4-dihydro-7-fluoro-2H-1-benzopyran-8-yl isocyanateYield 99.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

By the method of Example 1, Step F, 2.2 grams (0.011 mole) of 8-amino-5-chloro-3,4-dihydro-7-fluoro-2H-1-benzopyran and 2.2 grams (0.011 mole) of trichloromethyl chloroformate were reacted in 50 mL of toluene, yielding about 2.5 grams of 5-chloro-3,4-dihydro-7-fluoro-2H-1-benzopyran-8-yl isocyanate. The product was taken to the next step without further characterization.

Sources & evidence

ORD record
ord-b7d53091fdd84250941e45a98eafb287
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

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