Methanol → HCID 86739445, compound

HRID 1262618Notes

Reaction equation

HRID 1262618 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][C:5]([NH:7][C:8](=[O:12])[CH2:9][NH:10][CH3:11])=[O:6].[N:13]([O-])=[O:14].[Na+].CO>C(O)=O>[Cl:1][CH2:2][CH2:3][N:4]([N:13]=[O:14])[C:5]([NH:7][C:8](=[O:12])[CH2:9][NH:10][CH3:11])=[O:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 23668193Sodium NitriteHCID 86739446HCID 86739446, compound

Product 1

HCID 86739445HCID 86739445, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

N-[N'-(2-Chloroethyl)carbamoyl]sarcosine amide (100 mg, 0.516 mmol.) was dissolved in a 99% formic acid (0.7 ml) under ice-cooling, to which sodium nitrite (53.4 mg, 1.5 moles per mole of the starting compound) was slowly added and the mixture was held under stirring for further 30 minutes to complete the reaction. Then, Amberlite IR-120 (H+ form), a strongly acidic cation exchange resin made and sold by Rohm & Haas Company, (1 ml) and methanol (1 ml) were added to the resulting reaction solution and the mixture was stirred for 10 minutes. After the resin was removed by filtration, the reaction solution was concentrated in vacuo to leave an oily residue. The residue was purified by column chromatography on silica gel (Wako-gel C-300) with a developer system of toluene-ethanol (3:1 by volume), where the eluate was collected in fractions and the fractions containing the main product were collected together and concentrated in vacuo to afford N-[N'-(2-chloroethyl)-N'-nitrosocarbamoyl]sarcosine amide (62 mg) as a white crystalline residue.

Workup

  1. additionwas slowly added
  2. customthe reaction
  3. additionwere added to the resulting reaction solution
  4. stirringthe mixture was stirred for 10 minutes
  5. customAfter the resin was removed by filtration
  6. concentrationthe reaction solution was concentrated in vacuo
  7. customto leave an oily residue
  8. customThe residue was purified by column chromatography on silica gel (Wako-gel C-300) with a developer system of toluene-ethanol (3:1 by volume), where the eluate
  9. customwas collected in fractions
  10. additionthe fractions containing the main product
  11. customwere collected together
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9d5b2385b8534256a9de305b7cd3a2eb
Source dataset
uspto-grants-1984_06
Patent number
US04452814

Reaction notes

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