Triethylamine → 1-(2,4-Dichloro-3-chloromethylphenyl)-2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole

HRID 613611Notes

Reaction equation

HRID 613611 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8]O)=[C:6]([Cl:10])[CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH2:16][NH:17][C:18](=[O:31])[CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:30])[NH:28][CH3:29])=[CH:23][CH:22]=1.C(N(CC)CC)C.CS([Cl:43])(=O)=O>CN(C)C=O>[Cl:1][C:2]1[C:7]([CH2:8][Cl:43])=[C:6]([Cl:10])[CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH2:16][NH:17][C:18](=[O:31])[CH:19]=[CH:20][C:21]1[CH:22]=[CH:23][C:24]([C:27](=[O:30])[NH:28][CH3:29])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 539366561-(2,4-Dichloro-3-hydroxymethylphenyl)2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole

Product 1

HCID 536667761-(2,4-Dichloro-3-chloromethylphenyl)-2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 1-(2,4-dichloro-3-hydroxymethylphenyl)-2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole (148 mg), triethylamine (0.11 ml) and anhydrous dimethylformamide (1 ml) was added a 1M solution of methanesulfonyl chloride in dimethylformamide (0.77 ml) under ice-water cooling. The mixture was stirred at ambient temperature for 4 hours and partitioned between chloroform and saturated aqueous solution of sodium hydrogen carbonate. The organic layer was isolated, dried over magnesium sulfate and evaporated in vacuo to give a brown oil. The residue was purified by preparative thin layer chromatography (chloroform-methanol) to give 1-(2,4-dichloro-3-chloromethylphenyl)-2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole (120 mg) as an amorphous powder.

Workup

  1. custompartitioned between chloroform and saturated aqueous solution of sodium hydrogen carbonate
  2. customThe organic layer was isolated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customto give a brown oil
  6. customThe residue was purified by preparative thin layer chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-5cfbeaadd44e4013ba0acc6cfa48f266
Source dataset
uspto-grants-1999_12
Patent number
US06008229

Reaction notes

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