Anisole → HCID 86739894, compound

HRID 2413431Notes

Reaction equation

C([O:14][C:15]([CH2:17][C:18]([NH:20][C:21]1[N:22]2[CH:25]([S:26][CH2:27][C:28]=1[C:29]1[S:33][C:32]([NH:34][CH2:35][CH2:36][N:37]([CH3:39])[CH3:38])=[N:31][CH:30]=1)[CH:24]([S:40][C:41]1[CH:46]=[CH:45][C:44]([Cl:47])=[C:43]([Cl:48])[CH:42]=1)[C:23]2=[O:49])=[O:19])=[O:16])(C1C=CC=CC=1)C1C=CC=CC=1.C1(OC)C=CC=CC=1>C(O)=O>[C:15]([CH2:17][C:18]([NH:20][C:21]1[N:22]2[CH:25]([S:26][CH2:27][C:28]=1[C:29]1[S:33][C:32]([NH:34][CH2:35][CH2:36][N:37]([CH3:39])[CH3:38])=[N:31][CH:30]=1)[CH:24]([S:40][C:41]1[CH:46]=[CH:45][C:44]([Cl:47])=[C:43]([Cl:48])[CH:42]=1)[C:23]2=[O:49])=[O:19])([OH:16])=[O:14]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-benzhydryloxycarbonyl-7-(3,4-dichlorophenylthio)-acetamido-3-[2-(2-dimethylamino-ethylamino)-thiazol-5-yl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2ene (1.5 g), anisole (5 cc) and formic acid (25 cc) is stirred for 30 minutes at 50° C. The mixture is concentrated to dryness under reduced pressure (0.1 mm Hg; 0.013 kPa) and the residue is then taken up in ethanol (3×50 cc) and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C. The solid obtained is washed with acetone (50 cc) and then with ethyl ether (50 cc). It is dried under reduced pressure (0.1 mm Hg; 0.013 kPa), giving 2-carboxy-7-(3,4-dichloro-phenylthio)-acetamido-3-[2-(2-dimethylamino-ethylamino)-thiazol-5-yl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (1 g) in the form of a yellow powder.

Workup

concentrationThe mixture is concentrated to dryness under reduced pressure (0.1 mm Hg; 0.013 kPa)
concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C
customThe solid obtained
washis washed with acetone (50 cc)
customIt is dried under reduced pressure (0.1 mm Hg; 0.013 kPa)

Sources & evidence

ORD record: ord-d82355d90a064dc8a89c57dd8674117d
Source dataset: uspto-grants-1985_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04496560

Reaction notes

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