Acetic Anhydride → HCID 53976707, compound

HRID 1585976Notes

Reaction equation

HRID 1585976 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([CH:6]=[CH:7][C:8]2[C:14]3[CH:15]=[C:16]4[O:21][CH2:20][O:19][C:17]4=[CH:18][C:13]=3[CH2:12][C:11]([CH3:22])=[N:10][N:9]=2)=[CH:4][CH:3]=1.[C:25](OC(=O)C)(=[O:27])[CH3:26]>>[C:25]([NH:1][C:2]1[CH:24]=[CH:23][C:5]([CH:6]=[CH:7][C:8]2[C:14]3[CH:15]=[C:16]4[O:21][CH2:20][O:19][C:17]4=[CH:18][C:13]=3[CH2:12][C:11]([CH3:22])=[N:10][N:9]=2)=[CH:4][CH:3]=1)(=[O:27])[CH3:26]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 53676929HCID 53676929, compound

Product 1

HCID 53976707HCID 53976707, compound

Procedure

4.0 g (12.5 mmoles) of 1-(4-aminostyryl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine (the compound of Example 68) are suspended in 20 ml of acetic anhydride. The suspension is stirred at room temperature for 1 hour. In the meantime the starting substance gets dissolved, the desired product begins to separate and the reaction mixture becomes thick. The separated product is filtered, washed three times with 25 ml each of diethyl ether and dried at a temperature between 80° C. and 100° C. Thus 4.0 g of the desired product are obtained. In order to purify the crude product it is boiled in 15 ml of 50% ethanol for 15 minutes, cooled, filtered, washed three times with 5 ml each of 50% ethanol and dried at a temperature between 80° C. and 100° C. Thus 3.87 g (85.6%) of the desired product are obtained. M.p.: 218-220° C. (decomp.).

Workup

  1. dissolutionIn the meantime the starting substance gets dissolved

Sources & evidence

ORD record
ord-eafc2cd97b13448caee0b55412e52567
Source dataset
uspto-grants-1999_08
Patent number
US05942506

Reaction notes

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