Trichloroacetyl chloride → 183268-72-6

HRID 655765Notes

Reaction equation

HRID 655765 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][CH:6]=1.[Cl:7][C:8]([Cl:13])([Cl:12])[C:9](Cl)=[O:10].C([O-])([O-])=O.[K+].[K+]>C(OCC)C>[Cl:7][C:8]([Cl:13])([Cl:12])[C:9]([C:4]1[NH:3][C:2]([CH3:1])=[CH:6][CH:5]=1)=[O:10]

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 11430Potassium CarbonateHCID 124892-Methylpyrrole2×

Product 1

HCID 1714571183268-72-6

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

2-Methyl-1H-pyrrole (Intermediate 31, 10 g, 0.123 mmol) in anhydrous diethyl ether (30 ml) was added dropwise over 1 h to a stirred solution of trichloroacetyl chloride (29 g, 0.16 mmol) in anhydrous Et2O (100 ml). The mixture was stirred for a further 1 h then K2CO3 (10 g/30 ml) was added slowly through a dropping funnel. The organic phase was dried over Na2SO4 and treated with decolorizing charcoal (3 g) for 30 min at room temperature. The resulting purple solution was concentrated and triturated with n-hexanes to give the title compound as a purple solid. (16.72 g). NMR (CDCl3): 2.36 (s, 3H), 6.04 (dd, 1H), 7.45 (dd, 1H), 10.344 (s, 1H).

Workup

  1. dry with materialThe organic phase was dried over Na2SO4
  2. additiontreated with decolorizing charcoal (3 g) for 30 min at room temperature
  3. concentrationThe resulting purple solution was concentrated
  4. customtriturated with n-hexanes

Sources & evidence

ORD record
ord-a4b4722cdac5477c85837a45c51facc3
Source dataset
uspto-grants-2011_12
Patent number
US08071605B2

Reaction notes

Loading…