Phosgene → HCID 13672663, compound

HRID 2309328Notes

Reaction equation

HRID 2309328 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-4bdc2f6fa050476b8468d84341d7a83e
Source dataset
uspto-grants-1987_09
Patent number
US04695310

Reaction notes

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