Acetic Acid → HCID 20074870, compound

HRID 1109545Notes

Reaction equation

HRID 1109545 reaction equation
[CH2:1]([NH:4][C:5]([C:7]1[CH:20]=[CH:19][C:18]2[S:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH:21]([CH3:28])[CH2:22][N:23]3[CH2:27][CH:26]=[CH:25][CH2:24]3)[C:9]=2[CH:8]=1)=S)[CH:2]=[CH2:3].C(O)(=[O:31])C>>[CH2:1]([NH:4][C:5]([C:7]1[CH:20]=[CH:19][C:18]2[S:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH:21]([CH3:28])[CH2:22][N:23]3[CH2:27][CH:26]=[CH:25][CH2:24]3)[C:9]=2[CH:8]=1)=[O:31])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 176Acetic Acid2×HCID 20074875HCID 20074875, compound

Product 1

HCID 20074870HCID 20074870, compound

Procedure

The procedure is as described in Example 17, but starting with N-allyl-10-[1-(2,5-dihydro-1-pyrrolyl)-2-propyl]-2-phenothiazinecarbothioamide, L series (1.49 g), in acetic acid (25 cc) and a solution of mercuric acetate (1.16 g) in acetic acid (25 cc). The yellow meringue-like residue (1.27 g) is purified by chromatography on a column (height: 23 cm; diameter: 2.6 cm) of silica gel (0.04-0.63 mm) under a slight excess pressure of nitrogen (40 kPa), eluting with ethyl acetate (1.5 liters) and collecting 25-cc fractions. Fractions 10 to 58 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to give N-allyl-10-[1-(2,5-dihydro-1-pyrrolyl)-2-propyl]-2-phenothiazine-carboxamide, L series (0.45 g), in the form of a yellow resin.

Workup

  1. customThe yellow meringue-like residue (1.27 g) is purified by chromatography on a column (height: 23 cm; diameter: 2.6 cm) of silica gel (0.04-0.63 mm) under a slight excess pressure of nitrogen (40 kPa)
  2. washeluting with ethyl acetate (1.5 liters)
  3. customcollecting 25-cc fractions
  4. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.

Sources & evidence

ORD record
ord-ae1afeb6ffb74d2b94cba625e91f91df
Source dataset
uspto-grants-1994_06
Patent number
US05321026

Reaction notes

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