4-Toluenesulfonyl chloride → HCID 21966516, compound

HRID 2212490Notes

Reaction equation

HRID 2212490 reaction equation
C(N(C(C)C)CC)(C)C.[S:10](Cl)([C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1)(=[O:12])=[O:11].[OH:21][C:22]1[CH:26]=[CH:25][NH:24][C:23]=1[C:27]([O:29][CH3:30])=[O:28]>C(Cl)Cl>[S:10]([O:21][C:22]1[CH:26]=[CH:25][NH:24][C:23]=1[C:27]([O:29][CH3:30])=[O:28])([C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1)(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 54711834Methyl 3-hydroxy-1H-pyrrole-2-carboxylate

Product 1

HCID 21966516HCID 21966516, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diisopropylethylamine (7.1 mL, 40.7 mmole) and then a solution of TsCl (6.46 gm, 33.9 mole) in dry DCM (20 mL) were added to an ice-cooled solution of methyl 3-hydroxy-1H-pyrrole-2-carboxylate (4.78 gm; 33.9 mmole) in dry DCM (80 mL) under a dry N2 atmosphere. After 2 hr, the reaction was removed from the bath and allowed to warm to RT. After 2 hr, this was washed with water, dried (Na2SO4), and the solvents removed to leave methyl 3-(tosyloxy)-1H-pyrrole-2-carboxylate (10 gm) as a solid. 1H NMR (CDCl3): 2.39 (s, 3H), 3.64 (s, 3H), 6.06 (m, 1H), 6.75 (m, 1H), 7.26 (m, 2H), 7.71 (m, 2H); MS: 311(M+H)+; HPLC Ret Time: 1.28 min (YMC Xterra S7 3.0×50 mm column, 2 min gradient, 5 mL/min).

Workup

  1. customthe reaction was removed from the bath
  2. waitAfter 2 hr
  3. washthis was washed with water
  4. dry with materialdried (Na2SO4)
  5. customthe solvents removed

Sources & evidence

ORD record
ord-af93ba11d2e6454f826dcf941204c4c9
Source dataset
uspto-grants-2006_09
Patent number
US07102003B2

Reaction notes

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