2-Thiophenecarbonyl chloride → Anthrimide

HRID 622839

Reaction equation

HRID 622839 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([C:9]3[C:14]([C:15](=[O:16])[C:4]2=[CH:3][CH:2]=1)=[C:13]([NH:17][C:18]1[CH:23]=[CH:22][C:21](N)=[C:20]2[C:25]([C:27]4[C:32]([C:33](=[O:34])[C:19]=12)=[CH:31][CH:30]=[CH:29][CH:28]=4)=[O:26])[CH:12]=[CH:11][C:10]=3N)=[O:8].S1C=CC=C1C(Cl)=O>[N+](C1C=CC=CC=1)([O-])=O>[CH:1]1[CH:6]=[C:5]2[C:7]([C:9]3[CH:10]=[CH:11][CH:12]=[C:13]([NH:17][C:18]4[C:19]5[C:33]([C:32]6[C:27]([C:25](=[O:26])[C:20]=5[CH:21]=[CH:22][CH:23]=4)=[CH:28][CH:29]=[CH:30][CH:31]=6)=[O:34])[C:14]=3[C:15](=[O:16])[C:4]2=[CH:3][CH:2]=1)=[O:8]

Participants

4

Reactant 2

HCID 789282-Thiophenecarbonyl chlorideHCID 178507708HCID 178507708, compound

Product 1

HCID 6700AnthrimideYield 145.4%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

9.2 g of 4,4'-diamino-1,1'-dianthrimide are heated in 75 ml of nitrobenzene to 145°-150° C. 6.5 g of thiophene-2-carboxylic acid chloride are then added dropwise over a period of 30 minutes. The temperature of the suspension is increased to 170°-175° C. over a period of 2 hours and the suspension is stirred for 2 hours at that temperature. After cooling, the product is filtered off and washed with nitrobenzene and ethanol. 12.5 g of the anthrimide of the formula (2) are obtained. The anthrimide is converted into the carbazole compound of the formula (1) in accordance with Example 1, paragraph 2.

Workup

  1. temperatureThe temperature of the suspension is increased to 170°-175° C. over a period of 2 hours
  2. temperatureAfter cooling
  3. filtrationthe product is filtered off
  4. washwashed with nitrobenzene and ethanol

Sources & evidence

ORD record
ord-d0f4e1a4b9214e4f98160dd267039cb7
Source dataset
uspto-grants-1988_09
Patent number
US04772725

Linked notes

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