Potassium Carbonate → HCID 22902281, compound

HRID 1489778Notes

Reaction equation

[C:1]([C:4]1[NH:5][C:6]([CH3:13])=[C:7]([C:10](=[O:12])[CH3:11])[C:8]=1[CH3:9])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].S(Cl)([Cl:23])(=O)=O>ClCCl>[Cl:23][CH2:13][C:6]1[NH:5][C:4]([C:1](=[O:3])[CH3:2])=[C:8]([CH3:9])[C:7]=1[C:10](=[O:12])[CH3:11]

Participants

Conditions

Temperature: 0.5 °C

Procedure

To a stirred mixture of 2,4-diacetyl-3,5-dimethylpyrrole (1.0 g), dichloromethane (35 cm3) and potassium carbonate (7.73 g) at 0°-5° C. was added a solution of sulphuryl chloride (0.79 g) in dichloromethane (15 cm3). The temperature of the mixture was maintained at 0.5° C. during the addition by external cooling and then the mixture was stirred at this temperature until adjudged complete by t.l.c. (ca 2 h). The mixture was then filtered and evaporated to give crude 2-chloromethyl-3,5-diacetyl-4-methylpyrrole. This material was dissolved in acetic acid (10 cm3), sodium acetate (1.83 g) added, and then more acetic acid (10 cm3) added. The mixture was stirred overnight at room temperature, evaporated in vacuo, and the residue stirred with ice-cold water for 2 h. A solid was collected by filtration and the filtrate extracted twice with ethyl acetate. The extracts were dried (MgSO4), evaporated and the residue combined with the solid above, to give the crude product. Chromatography on silica eluting with ethyl acetate-hexane (1:1) gave 0.075 g. of pure product as an off-white solid m.p. 112.5°-114.5° C.; m/z 238 (M+ +1, FAB), δH, CDCl3) 2.16 (3H, s, OCOCH3), 2.50 (3H, s, CH3), 2.53 (3H, s, CH3), 2.62 (3H, s, CH3), 5.38 (2H, s, OCH2).

Workup

temperatureby external cooling
custom(ca 2 h)
filtrationThe mixture was then filtered
customevaporated

Sources & evidence

ORD record: ord-085611d450124c829c0ca355506497e0
Source dataset: uspto-grants-1997_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05679694

Reaction notes

Loading…