Phosgene → 1-Methyl-1H-benzotriazole-4-sulfonylisocyanate

HRID 1722197Notes

Reaction equation

HRID 1722197 reaction equation
C(N[C:6]([NH:8][S:9]([C:12]1[C:20]2[N:19]=[N:18][N:17]([CH3:21])[C:16]=2[CH:15]=[CH:14][CH:13]=1)(=[O:11])=[O:10])=[O:7])CCC.N12CCN(CC1)CC2.C(Cl)(Cl)=O>>[CH3:21][N:17]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([S:9]([N:8]=[C:6]=[O:7])(=[O:11])=[O:10])[C:20]=2[N:19]=[N:18]1

Participants

4

Reactant 3

HCID 6371PhosgeneHCID 9237DabcoHCID 14180041N-[(Butylamino)carbonyl]-1-methyl-1H-benzotriazole-4-sulfonamide

Product 1

HCID 141800421-Methyl-1H-benzotriazole-4-sulfonylisocyanateYield 48.3%

Procedure

To a stirred mixture of N-[(butylamino)carbonyl]-1-methyl-1H-benzotriazole-4-sulfonamide (8.25 g), 1,4-diazabicyclo[2,2,2]octane (catalytic amount), and xylenes (175 mL), heated at reflux under a nitrogen atmosphere, was added phosgene (2 mL) in small portions over 1 hour. The resulting suspension was heated an additional 0.5 hours and was cooled prior to filtering off the insoluble material. The filtrate was evaporated to give 3.05 g of the title compound as a pale yellow solid. IR (nujol) 2260 cm-1. The compound was immediately diluted to 100 mL with dry acetonitrile and stored under nitrogen to give a 0.125M solution of the title compound for further use.

Workup

  1. temperatureheated
  2. temperatureat reflux under a nitrogen atmosphere
  3. temperatureThe resulting suspension was heated an additional 0.5 hours
  4. temperaturewas cooled
  5. filtrationto filtering off the insoluble material
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-d46829a141e943059cecc6a5631f0daa
Source dataset
uspto-grants-1989_08
Patent number
US04854962

Reaction notes

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