Phosgene → HCID 13672663, compound

HRID 1981273Notes

Reaction equation

HRID 1981273 reaction equation
[CH3:1][C:2]1([CH3:15])[S:6][C:5]2[C:7]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:8][CH:9]=[CH:10][C:4]=2[CH2:3]1.C(N=[C:21]=[O:22])CCC.C1N2CCN(CC2)C1.C(Cl)(Cl)=O>>[CH3:1][C:2]1([CH3:15])[S:6][C:5]2[C:7]([S:11]([N:14]=[C:21]=[O:22])(=[O:13])=[O:12])=[CH:8][CH:9]=[CH:10][C:4]=2[CH2:3]1

Participants

5

Reactant 4

HCID 6371PhosgeneHCID 8110Butyl isocyanateHCID 9237DabcoHCID 13424189HCID 13424189, compound

Product 1

HCID 13672663HCID 13672663, compound

Procedure

To a refluxing solution of 8.6 g of 2,3-dihydro-2,2-dimethyl-7-benzo[b]thiophenesulfonamide (Example 14), 4.0 ml of n-butylisocyanate and 0.1 g of DABCO in 100 ml of xylenes was added 3.0 ml of phosgene at such a rate that the reaction temperature did not drop below 135° C. The mixture was refluxed for 1.5 hours, then the excess phosgene was purged with a stream of dry nitrogen. The mixture was cooled, filtered and concentrated in vacuo to yield the title compound as an oil. The crude yield was assumed to be near quantitative. IR (neat) 2220 cm-1 (NCO).

Workup

  1. customdid not drop below 135° C
  2. temperatureThe mixture was refluxed for 1.5 hours
  3. customthe excess phosgene was purged with a stream of dry nitrogen
  4. temperatureThe mixture was cooled
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cab5d733b9c345a29f0cd1a87a4174bc
Source dataset
uspto-grants-1985_04
Patent number
US04514211

Reaction notes

Loading…