Benzoyl chloride, 3-nitro- → HCID 86742197, compound

HRID 1253247Notes

Reaction equation

[CH3:1][C@@H:2]([C@@H:10]1[C@@:14]2([CH3:31])[CH2:15][CH2:16][C@@:17]34[CH2:23][C@:22]53[CH2:24][CH2:25][C@H:26]([OH:30])[C:27]([CH3:29])([CH3:28])[C@@H:21]5[CH2:20][CH2:19][C@H:18]4[C@:13]2([CH3:32])[CH2:12][CH2:11]1)[CH2:3][CH2:4][C:5]([CH3:9])=[C:6]([CH3:8])[CH3:7].[N+:33]([C:36]1[CH:37]=[C:38]([CH:42]=[CH:43][CH:44]=1)[C:39](Cl)=[O:40])([O-:35])=[O:34]>N1C=CC=CC=1>[CH3:1][C@@H:2]([C@@H:10]1[C@@:14]2([CH3:31])[CH2:15][CH2:16][C@@:17]34[CH2:23][C@:22]53[CH2:24][CH2:25][C@H:26]([OH:30])[C:27]([CH3:29])([CH3:28])[C@@H:21]5[CH2:20][CH2:19][C@H:18]4[C@:13]2([CH3:32])[CH2:12][CH2:11]1)[CH2:3][CH2:4][C:5]([CH3:9])=[C:6]([CH3:7])[CH3:8].[N+:33]([C:36]1[CH:37]=[C:38]([CH:42]=[CH:43][CH:44]=1)[C:39]([O-:30])=[O:40])([O-:35])=[O:34]

Participants

Conditions

Temperature: 20 °C

Procedure

Cyclobranol (18 g, 0.04 mole) dissolved in pyridine (200 ml) was stirred and cooled in a bath of ice water, and to it was added m-nitrobenzoyl chloride (9.85 g, 0.053 mole). Then the mixture was warmed to 20° C. and continued to stir for 12 hours. After the reaction is complete the mixture was evaporated under reduced pressure. Ice cold water (200 ml) was added to the residue and crystals begans to appear. The crude crystals were separated by filtration and recrystallized from acetone-water (1:1, V/V), giving cyclobranol-m-nitrobenzoate (20.1 g), in a 83% yield. m.p. 206°-207° C.

Workup

stirringto stir for 12 hours
customwas evaporated under reduced pressure
additionIce cold water (200 ml) was added to the residue and crystals
customThe crude crystals were separated by filtration
customrecrystallized from acetone-water (1:1, V/V)

Sources & evidence

ORD record: ord-d562b69e6295487ca7c7b23d0697a100
Source dataset: uspto-grants-1988_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04748161

Reaction notes

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