Dimethylformamide → HCID 22641001, compound

HRID 2415274Notes

Reaction equation

HRID 2415274 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=S.[CH2:13]([N:15]([CH2:28][CH3:29])[CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=1)[CH3:14].CN(C)[CH:32]=[O:33]>>[CH2:13]([N:15]([CH2:28][CH3:29])[CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:32]=[O:33])=[CH:21][CH:20]=1)[CH3:14]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 802641,1'-ThiocarbonyldiimidazoleHCID 88294Diethyl[2-(4-nitrophenoxy)ethyl]amine

Product 1

HCID 22641001HCID 22641001, compoundYield 83%

Conditions

Temperature
-15 °C

Procedure

Thiocarbonyldiimidazole (4.56 g, 25.6 mmol) (Aldrich) was dissolved in N,N-dimethylformamide (25 mL) and the solution cooled to −15° C. A solution diethyl-[2-(4-nitro-phenoxy)-ethyl]-amine (5 g, 25.7 mmol) (from Step B above) in N,N-dimethylformamide (75 mL) was added dropwise and the mixture was then stirred at room temperature for 1 hour. The solution was cooled to 0° C. and poured into ice/water (1000 mL), stirred 30 minutes, and the precipitate was filtered off, washed with water and dried under high vacuum to give 4.95 g, (83%) diethyl-[2-(4-isocyanato-phenoxy)-ethyl]-amine. Mass spectrum (ES) MH+=251.

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. stirringstirred 30 minutes
  3. filtrationthe precipitate was filtered off
  4. washwashed with water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-46d2dd5dc13447a48fdf29ad4ac15e99
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

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