Methyl iodide → HCID 13421472, compound

HRID 580315Notes

Reaction equation

HRID 580315 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:16][C:17](=[O:22])[O:18][CH:19]([CH3:21])[CH3:20])[CH:7]=[C:8]([O:13][CH2:14][CH3:15])[C:9]=1[O:10][CH2:11][CH3:12])([O-:3])=[O:2].I[CH3:24].[OH-].[K+]>O1CCCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:24][N:16]([C:6]1[CH:7]=[C:8]([O:13][CH2:14][CH3:15])[C:9]([O:10][CH2:11][CH3:12])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[C:17](=[O:22])[O:18][CH:19]([CH3:20])[CH3:21]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 13421414Propan-2-yl (3,4-diethoxy-5-nitrophenyl)carbamate

Product 1

HCID 13421472HCID 13421472, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Isopropyl N-(3-nitro-4,5-diethoxyphenyl)carbamate (3.12 g) and iodomethane (4.30 g) were dissolved in tetrahydrofuran (10 ml). The resultant solution was dropwise added to a tetrahydrofuran solution containing potassium hydroxide (1.68 g) and tetra-n-butylammonium bromide (1.0 g). After being allowed to stand at room temperature for 12 hours, the reaction mixture was poured into ice-water and extracted with toluene. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The reside was purified by silica gel chromatography using a mixture of toluene and ethyl acetate as the eluent to give isopropyl N-methyl-N-(3-nitro-4,5-diethoxyphenyl)carbamate (Compound No. 161) (2.92 g) in a yield of 89.5%. nD20.0 1.5075.

Workup

  1. extractionextracted with toluene
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe reside was purified by silica gel chromatography
  6. additiona mixture of toluene and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-c213af7fe7164e8788ba345e61a735a3
Source dataset
uspto-grants-1988_06
Patent number
US04752615

Reaction notes

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