N-methyl-2-pyrrolidone → HCID 21191975, compound

HRID 1957796Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([S:10]([N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C[N:19]1[CH2:23][CH2:22][CH2:21][C:20]1=O.[OH:25][C:26]1[C:35]([C:36](Cl)=[O:37])=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[C:31]([C:39](Cl)=[O:40])[CH:32]=2)[CH:27]=1>C1(C)C=CC=CC=1>[OH:25][C:26]1[C:35]([C:36]([NH:1][C:2]2[CH:3]=[C:4]([S:10]([N:13]([CH2:14][CH3:15])[CH2:16][CH3:17])(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=2[O:8][CH3:9])=[O:37])=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[C:31]([C:39]([NH:19][C:23]3[CH:22]=[C:21]([S:10]([N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])(=[O:11])=[O:12])[CH:20]=[CH:2][C:7]=3[O:8][CH3:9])=[O:40])[CH:32]=2)[CH:27]=1

Participants

Conditions

Temperature: 25 °C

Procedure

3-Amino-4-methoxydiethylaminosulfonylbenzene (15.6 g), N-methyl-2-pyrrolidone (86.1 g) and toluene (34.3 g) were dissolved at room temperature and the acid chloride (5.4 g) obtained in Example 6 was gradually added, and then the mixture was amidated at 90° C. for 24 hours. After the reaction solution was cooled to 25° C. and filtered, toluene was distilled off under reduced pressure. Then, the solution was crystallized by using methanol (350.1 g). The resultant product was filtered and then dried to obtain 8.9 g of 2-hydroxy-3,6-bis(2-methoxy-5-diethylaminosulfonylphenyl-aminocarbonyl)naphthalene as a cream powdered crystal (DSC analysis value: 245.0° C.).

Workup

filtrationfiltered
distillationtoluene was distilled off under reduced pressure
customThen, the solution was crystallized
filtrationThe resultant product was filtered
customdried

Sources & evidence

ORD record: ord-2d1688f5e631421c8b81f8094aa1a520
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05786523

Reaction notes

Loading…