Phosgene → HCID 18916386, compound

HRID 1290635Notes

Reaction equation

HRID 1290635 reaction equation
[C:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[C:14]2[S:13][C:12]([Cl:15])=[N:11][C:10]=2[C:9]([Cl:16])=[CH:8][C:7]=1[Cl:17]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:15][C:12]1[S:13][C:14]2[C:6]([N:5]=[C:1]=[O:2])=[C:7]([Cl:17])[CH:8]=[C:9]([Cl:16])[C:10]=2[N:11]=1

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 18916431HCID 18916431, compound

Product 1

HCID 18916386HCID 18916386, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Under a nitrogen atmosphere 25 mL of ethyl acetate was stirred and cooled in an ice bath. To this was added via syringe 9.5 mL (18 mmole) of 1.9M phosgene in toluene. During 25 minutes, a solution of 3.0 grams (11.8 mmole) of 7-amino-2,4,6-trichlorobenzothiazole in 75 mL of ethyl acetate was added dropwise. Upon completion of the addition the reaction mixture was warmed to ambient temperature and then gently heated at reflux for 2.5 hours. After this time the reaction mixture was concentrated under reduced pressure, yielding (2,4,6-trichlorobenzothiazol-7-yl)isocyanate, which was stored in a refrigerator.

Workup

  1. temperaturecooled in an ice bath
  2. additionUpon completion of the addition the reaction mixture
  3. temperaturegently heated
  4. temperatureat reflux for 2.5 hours
  5. concentrationAfter this time the reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-39256ecd2ce746b994e63caae6cf18f6
Source dataset
uspto-grants-1998_05
Patent number
US05753595

Reaction notes

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