2-(Methylamino)ethanol → HCID 20385347, compound

HRID 46724Notes

Reaction equation

HRID 46724 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]=[O:12])=[CH:6][C:5]=1[C:13]([F:16])([F:15])[F:14])([O-:3])=[O:2].[CH3:17][NH:18][CH2:19][CH2:20][OH:21]>O1CCCC1>[OH:21][CH2:20][CH2:19][N:18]([CH3:17])[C:11]([NH:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([C:13]([F:14])([F:15])[F:16])[CH:6]=1)=[O:12]

Participants

4

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 153425614-Isocyanato-1-nitro-2-(trifluoromethyl)benzene

Product 1

HCID 20385347HCID 20385347, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 46.4 g (0.2 mol) of 4-nitro-3-(trifluoromethyl)phenyl isocyanate in 200 ml of tetrahydrofuran was added dropwise with stirring and external cooling 15.2 g (0.2 mol) of 2-(methylamino)ethanol. This addition was exothermic. The solution was concentrated under reduced pressure, washed with water, acidified with hydrochloric acid and extracted with ether. Crystallization of the ether extract gave 43.69 g (71% yield) of the desired product as a tan solid; m.p. 180°-181° C.

Workup

  1. additionThis addition
  2. concentrationThe solution was concentrated under reduced pressure
  3. washwashed with water
  4. extractionextracted with ether
  5. customCrystallization of the ether
  6. extractionextract

Sources & evidence

ORD record
ord-e65ceb771ef34402ac8f651c94b1f646
Source dataset
uspto-grants-1979_11
Patent number
US04174958

Reaction notes

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