Toluene → Methyl 1-methyl-5-sulfamoyl-1h-pyrrole-2-carboxylate

HRID 331184Notes

Reaction equation

HRID 331184 reaction equation
[NH2:1][S:2]([C:5]1[N:9]([CH3:10])[C:8]([C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:14]1(C)C=CC=CC=1.C[Si](C=[N+]=[N-])(C)C>CO>[NH2:1][S:2]([C:5]1[N:9]([CH3:10])[C:8]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 1140TolueneHCID 167693Trimethylsilyldiazomethane2×HCID 27430181-Methyl-5-sulphamoyl-1H-pyrrole-2-carboxylic acid

Product 1

HCID 2743016Methyl 1-methyl-5-sulfamoyl-1h-pyrrole-2-carboxylateYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(Aminosulfonyl)-1-methyl-1H-pyrrole-2-carboxylic acid (1310 mg; 6.42 mmol; 1 eq.), commercially available (ASDI), is dissolved in MeOH (24 ml), then toluene (8 ml) is added followed by the dropwise addition of (trimethylsilyl)diazomethane (9.62 ml; 2M; 19.25 mmol; 3 eq). The solution is stirred at r.t. for 2 hr and another equivalent of (trimethylsilyl)diazomethane (3.21 ml; 2 M; 6.42 mmol; 1 eq) is added to reaction mixture. After 1 hr stirring, the solvent is concentrated to dryness and the resulting off white solid is recrystallized in MeOH to afford 851.1 mg (61%) of the title compound. 1H NMR (DMSO-d6) δ 7.58 (d, J=1.5 Hz, 1H), 7.13 (s, 2H), 7.06 (d, J=1.9 Hz, 1H), 3.88 (s, 3H), 3.77 (s, 3H). HPLC (max plot) 100%; Rt 1.19 min. LC/MS: (ES−) 217.1.

Workup

  1. stirringAfter 1 hr stirring
  2. concentrationthe solvent is concentrated to dryness
  3. customthe resulting off white solid is recrystallized in MeOH

Sources & evidence

ORD record
ord-bb19e32ec21044bfb9f43d6c6e2bac38
Source dataset
uspto-grants-2014_11
Patent number
US08877757B2

Reaction notes

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