Hexane → N-(2-Chloro-6-methanesulfonylmethyl-phenyl)-formimidic acid methyl ester

HRID 23390Notes

Reaction equation

HRID 23390 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])[C:3]=1[NH2:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:26]([O:29][CH2:30]C)(=O)C.CCCCCC>C(OC)(OC)OC>[CH3:26][O:29][CH:30]=[N:13][C:3]1[C:4]([CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 225740912-Chloro-6-methanesulfonylmethyl-phenylamine

Product 1

HCID 69545940N-(2-Chloro-6-methanesulfonylmethyl-phenyl)-formimidic acid methyl ester

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Procedure

The 2-chloro-6-methanesulfonylmethyl-phenylamine (2.04 g, 0.019 mole) of Step 4 was suspended in 15 ml trimethyl orthoformate and p-toluenesulfonic acid hydrate (0.21 g) was added. The reaction mixture was brought to reflux and heated at this temperature for 3 h. The reaction was monitored by tlc (3:7 ethyl acetate:hexane, silica gel) which showed the appearance of a new slightly less polar spot. At the end of 3 h, the reaction was cooled and evaporated to dryness to afford N-(2-Chloro-6-methanesulfonylmethyl-phenyl)-formimidic acid methyl ester.

Workup

  1. temperatureto reflux
  2. temperatureheated at this temperature for 3 h
  3. temperatureAt the end of 3 h, the reaction was cooled
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-0668754525574672803c0c12c2c5681b
Source dataset
uspto-grants-2005_02
Patent number
US06852726B2

Reaction notes

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