Formaldehyde → HCID 9909016, compound

HRID 1585082Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)=[CH:11][CH:10]=[C:9]2[CH3:23])=[CH:4][CH:3]=1.C=O.[OH-].[Na+].CCCCCC.[C:34]([O:37][CH2:38]C)(=[O:36])[CH3:35]>CC(O)=O>[C:34]([O:37][CH2:38][C:10]1[CH:11]=[C:12]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:9]=1[CH3:23])(=[O:36])[CH3:35]

Participants

Conditions

Temperature: 52.5 °C

Procedure

To a solution of 1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole (Example 1) (500 mg, 2.87 mmol) in AcOH (5 ml), formaldehyde (0.22 ml, 40% solution in water, 2.87 mmol) was added. After heating at 50-55° C. for 90 minutes, the reaction mixture was cooled and poured over ice. The solution was made alkaline with 2N NaOH and extracted with methylene chloride. The organic fractions were washed with water and with brine, dried (MgSO4), filtered and concentrated to give the crude product (780 mg) as a yellowish liquid. Chromatography (silica gel, hexane/ethyl acetate, 6/4) gave [1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrol-3-yl]methyl acetate (250 mg, 22%) as a white solid: mp (DSC) 151° C. Anal Calc'd. for C21H20NSFO4 : C, 62.83; H, 5.02; N, 3.49. Found: C, 62.48; H, 5.16; N, 3.37.

Workup

temperaturethe reaction mixture was cooled
additionpoured over ice
extractionextracted with methylene chloride
washThe organic fractions were washed with water and with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customto give the crude product (780 mg) as a yellowish liquid

Sources & evidence

ORD record: ord-908bf776398d46ab81ea73158a7012f0
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05935990

Reaction notes

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