Phosgene → HCID 13282662, compound

HRID 904773Notes

Reaction equation

HRID 904773 reaction equation
C(N[C:6]([NH:8][S:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19]([CH3:22])(=[O:21])=[O:20])(=[O:11])=[O:10])=[O:7])CCC.N12CCN(CC1)CC2.C(Cl)(Cl)=O>>[CH3:22][S:19]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][S:9]([N:8]=[C:6]=[O:7])(=[O:10])=[O:11])(=[O:20])=[O:21]

Participants

4

Reactant 3

HCID 6371PhosgeneHCID 9237DabcoHCID 13282669HCID 13282669, compound

Product 1

HCID 13282662HCID 13282662, compound

Conditions

Temperature
125 °C

Procedure

A suspension of 5.5 g of the product from Example 9 and 0.1 g of 1,4-diazabicyclo[2.2.2]octane (DABCO) in 100 ml dry xylenes was heated to 125°-130° C. under an atmosphere of nitrogen. At this temperature, 2.5 ml of phosgene was added dropwise at a rate that maintained the temperature above 120° C. After completion of the addition (ca. one hour), the solution was heated at 125° C. for another two hours. After cooling to room temperature, the mixture was filtered under nitrogen and concentrated in vacuo to afford crude 2-(methylsulfonyl)phenylmethanesulfonyl isocyanate as a yellow semisolid which was carried on to the next step without purification. The IR spectrum of this intermediate displayed a characteristic isocyanate absorption at 2240 cm-1.

Workup

  1. temperaturewas heated to 125°-130° C. under an atmosphere of nitrogen
  2. temperaturemaintained the temperature above 120° C
  3. additionAfter completion of the addition (ca. one hour)
  4. temperatureAfter cooling to room temperature
  5. filtrationthe mixture was filtered under nitrogen
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3d4d78c02c9540618a7ce216d0eb9925
Source dataset
uspto-grants-1983_12
Patent number
US04420325

Reaction notes

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