4-Butylbenzoyl chloride → HCID 14745971, compound

HRID 2106977Notes

Reaction equation

[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([NH2:18])=[CH:4][C:3]=1[CH2:19][CH2:20][CH2:21][CH3:22].[CH2:23]([C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1)[CH2:24][CH2:25][CH3:26]>ClC1C=CC=CC=1>[CH2:23]([C:27]1[CH:35]=[CH:34][C:30]([C:31]([NH:1][C:2]2[C:15]3[C:14](=[O:16])[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[C:7](=[O:17])[C:6]=3[C:5]([NH:18][C:7](=[O:17])[C:6]3[CH:15]=[CH:2][C:3]([CH2:19][CH2:20][CH2:21][CH3:22])=[CH:4][CH:5]=3)=[CH:4][C:3]=2[CH2:19][CH2:20][CH2:21][CH3:22])=[O:32])=[CH:29][CH:28]=1)[CH2:24][CH2:25][CH3:26]

Participants

Conditions

Temperature: 20 °C

Procedure

1,4-Diamino-2-butylanthraquinone (0.30 g, 0.001 mole) and p-butylbenzoic acid chloride (0.48 g, 0.0024 mole) are refluxed in 20 ml chlorobenzene for 0.5 hrs. The reaction mass is cooled to 20° C. and chromatographed with chloroform on Silica gel. 1,4-Bis(4-butylbenzamido)-2-butylanthraquinone is obtained in amount 0.36 g (60%). Found, %: C 76.74, H 8.31, N 4.53; C40H52N2O4. Calculated, %: C 76.89, H 8.39, N 4.48; λmax =475 nm, S=-0.22. M.p.=180°-181.3° C.

Workup

customchromatographed with chloroform on Silica gel

Sources & evidence

ORD record: ord-9b7f73bd5fb4436eb472b51777685777
Source dataset: uspto-grants-1990_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04933104

Reaction notes

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