tert-Butoxy bis(dimethylamino)methane → HCID 53887015, compound

HRID 1110363Notes

Reaction equation

HRID 1110363 reaction equation
[CH3:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].C(O[CH:18](N(C)C)[N:19]([CH3:21])[CH3:20])(C)(C)C>CN(C)C=O>[CH3:18][N:19]([CH3:21])[CH:20]=[CH:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6]

Participants

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 193730653-Methyl-2-nitrobenzonitrile

Product 1

HCID 53887015HCID 53887015, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-methyl-2-nitrobenzonitrile from Example 1c (5.72 g) and tert-butoxy-bis(dimethylamino)methane (9.5 ml) in dimethylformamide (30 ml) was heated to 90° with stirring for 1.5 hours. After cooling to ambient temperature the mixture was partitioned between ethyl acetate and water. The layers were separated with the aqueous phase further extracted using two portions of ethyl acetate. The combined ethyl acetate layer was washed with water then brine. The solution was dried over MgSO4 and filtered through a small pad of silica gel. After concentrating the material a very dark brown solid was obtained. Recrystallization from ethyl acetate/hexane gave the title product (6.99 g, 91%) as dark brown crystals.

Workup

  1. temperaturewas heated to 90°
  2. customwas partitioned between ethyl acetate and water
  3. customThe layers were separated with the aqueous phase
  4. extractionfurther extracted
  5. washThe combined ethyl acetate layer was washed with water
  6. dry with materialThe solution was dried over MgSO4
  7. filtrationfiltered through a small pad of silica gel
  8. concentrationAfter concentrating the material a very dark brown solid
  9. customwas obtained
  10. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-590d73ec1a3748398c6cc3a4520aa790
Source dataset
uspto-grants-1990_12
Patent number
US04975435

Reaction notes

Loading…