Phosgene → HCID 13341768, compound

HRID 2295387Notes

Reaction equation

HRID 2295387 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH3:5][S:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([NH2:17])(=[O:16])=[O:15].C1N2CCN(CC2)C1.C(N=C=O)CCC>C1(C)C(C)=CC=CC=1.C(Cl)Cl>[CH3:5][S:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([N:17]=[C:1]=[O:2])(=[O:16])=[O:15]

Participants

7

Reactant 4

HCID 6371PhosgeneHCID 8110Butyl isocyanateHCID 9237DabcoHCID 13057419HCID 13057419, compound

Product 1

HCID 13341768HCID 13341768, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7237O-XyleneSolvent

Procedure

Phosgene (2.5 ml, 35 mmol) was added portionwise into a nitrogen-purged mixture containing 6.8 g (31 mmol) of o-methylthiomethylbenzenesulfonamide, 0.1 g of DABCO, and 3.8 g (38 mmol) of n-butyl isocyanate in 60 ml of dry xylene, while the temperature was maintained at 130°-135° C. between additions. Stirring was continued for 1 hour at 130°-135° C. The mixture was cooled to room temperature and the solid was filtered off under nitrogen. The filtrate was concentrated to yield 9.0 g (theo 7.6 g) of oil: IR cm-1 2240 (N=C=O), no NH at ca 3300. The oil was taken up in 90 ml of dry methylene chloride.

Workup

  1. custompurged mixture
  2. temperaturewhile the temperature was maintained at 130°-135° C. between additions
  3. filtrationthe solid was filtered off under nitrogen
  4. concentrationThe filtrate was concentrated
  5. customto yield 9.0 g (theo 7.6 g) of oil

Sources & evidence

ORD record
ord-ee609bc66f0646d9b71497dce4e12260
Source dataset
uspto-grants-1984_01
Patent number
US04424377

Reaction notes

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