Diphosgene → Methyl 6-chloro-3-isocyanato-2-methylbenzoate

HRID 650906Notes

Reaction equation

HRID 650906 reaction equation
[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([C:9]([Cl:12])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Cl[C:15](OC(Cl)(Cl)Cl)=[O:16]>C1(C)C=CC=CC=1>[Cl:12][C:9]1[C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([CH3:13])[C:2]([N:1]=[C:15]=[O:16])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 21710154Methyl 3-amino-6-chloro-2-methylbenzoate

Product 1

HCID 21710153Methyl 6-chloro-3-isocyanato-2-methylbenzoateYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 14.7 grams (0.074 mole) of methyl 3-amino-6-chloro-2-methylbenzoate in 1000 mL of toluene was stirred and 14.6 grams (0.074 mole) of trichloromethyl chloroformate was added dropwise thereto. Upon completion of the addition, the reaction mixture was warmed to reflux where it stirred for about 18 hours. After this time the reaction mixture was concentrated under reduced pressure to a residue, which was assumed to be a theoretical yield (16.7 grams) of the subject compound. The subject compound was taken directly to the next reaction in the sequence.

Workup

  1. additionUpon completion of the addition
  2. temperaturethe reaction mixture was warmed
  3. temperatureto reflux where it
  4. concentrationAfter this time the reaction mixture was concentrated under reduced pressure to a residue, which

Sources & evidence

ORD record
ord-9d77af4b16114bcc9c5d2af4302d87ab
Source dataset
uspto-grants-2001_08
Patent number
US06277847B1

Reaction notes

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