Methyl iodide → HCID 20026632, compound

HRID 1723129Notes

Reaction equation

HRID 1723129 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[NH:9][C:10]([NH:12][CH2:13][CH:14]([O:17][CH3:18])[O:15][CH3:16])=[S:11])=[CH:4][C:3]=1[N+:25]([O-:27])=[O:26].IC.[C:30](=O)([O-])[O-].[K+].[K+]>CC(=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:9][C:10]([S:11][CH3:30])=[N:12][CH2:13][CH:14]([O:17][CH3:18])[O:15][CH3:16])=[CH:4][C:3]=1[N+:25]([O-:27])=[O:26]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 20026611HCID 20026611, compound

Product 1

HCID 20026632HCID 20026632, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(a-3) A mixture of 22.3 parts of (+)-N-[(4-amino-3-nitrophenyl)phenylmethyl]-N'-(2,2-dimethoxyethyl)thiourea, 10.2 parts of iodomethane, 11.8 parts of potassium carbonate and 240 parts of 2-propanone was stirred over weekend at room temperature. The reaction mixture was filtered over diatomaceous earth and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the elunet was evaporated, yielding 23 parts (100%) of (+)-methyl N-[(4-amino-3-nitrophenyl)phenylmethyl]-N'-(2,2-dimethoxyethyl)carbamimidothioate as a residue (141).

Workup

  1. filtrationThe reaction mixture was filtered over diatomaceous earth
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe elunet was evaporated

Sources & evidence

ORD record
ord-0a9cd21e22d643588d43b22a50fd27d0
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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