Isopropyl isocyanate → HCID 57659246, compound

HRID 38208Notes

Reaction equation

HRID 38208 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([CH3:13])(=[NH:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH:14]([N:17]=[C:18]=[O:19])([CH3:16])[CH3:15]>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([CH3:13])(=[N:12][C:18](=[O:19])[NH:17][CH:14]([CH3:16])[CH3:15])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanate3×HCID 596740531-(S-Methanesulfonimidoyl)-3-nitrobenzene

Product 1

HCID 57659246HCID 57659246, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
104 °C

Procedure

8.24 g (41.2 mmol) (RS)—S-(3-nitrophenyl)-S-methylsulfoximide in 370 ml toluene were treated with 13.6 ml (138.3 mmol) isopropyl isocyanate. The mixture was stirred under argon at 104° C. for 5 hours and at room temperature for 60 hours. 4.5 ml (46 mmol) isopropyl isocyanate were added and the mixture was stirred under argon at 104° C. for 6 hours and at room temperature for 16 hours. 4.5 ml (46 mmol) isopropyl isocyanate were added and the mixture was stirred under argon at 104° C. for 7 hours and at room temperature for 17 hours. The mixture was cooled with ice for 40 minutes. The suspension was filtrated to give 9.2 g (78% yield) of the product.

Workup

  1. stirringthe mixture was stirred under argon at 104° C. for 6 hours and at room temperature for 16 hours
  2. stirringthe mixture was stirred under argon at 104° C. for 7 hours and at room temperature for 17 hours
  3. temperatureThe mixture was cooled with ice for 40 minutes
  4. filtrationThe suspension was filtrated

Sources & evidence

ORD record
ord-4f5bca15a4b54f47903169cdecdd85c5
Source dataset
uspto-grants-2013_09
Patent number
US08524724B2

Reaction notes

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