Methyl iodide → HCID 13339720, compound

HRID 1905710Notes

Reaction equation

HRID 1905710 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([NH:17][C:18](=[O:23])[O:19][CH:20]([CH3:22])[CH3:21])[CH:7]=[C:8]([O:13][CH:14]([F:16])[F:15])[C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].I[CH3:25].[OH-].[K+]>O1CCCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:25][N:17]([C:6]1[CH:7]=[C:8]([O:13][CH:14]([F:16])[F:15])[C:9]([O:10][CH2:11][CH3:12])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=1)[C:18](=[O:23])[O:19][CH:20]([CH3:21])[CH3:22]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 13339716HCID 13339716, compound

Product 1

HCID 13339720HCID 13339720, compoundYield 89.9%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Isopropyl N-(3,4-diethoxy-5-difluoromethoxyphenyl)carbamate (3.33 g) and iodomethane (4.30 g) were dissolved in tetrahydrofuran (10 ml). The resultant solution was dropwise added to a 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 residue was purified by silica gel chromatography using a mixture of toluene and ethyl acetate as the eluent to give isopropyl N-methyl-N-(3,4-diethoxy-5-difluoromethoxyphenyl)carbamate (Compound No. 55) (3.12 g) in a yield of 89.8%.

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 residue was purified by silica gel chromatography
  6. additiona mixture of toluene and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-a954a1203f6f4e3798ea33d49fd66c79
Source dataset
uspto-grants-1987_03
Patent number
US04647582

Reaction notes

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