Ammonia → Ether 3-[4-(3-amino-5-bromopyrid-2-yl)butylamino]-4-amino-1,2,5-thiadiazole-1-oxide

HRID 371407Notes

Reaction equation

[NH2:1][C:2]1[C:3]([CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]2[C:18]([O:19][CH3:20])=[N:17][S:16](=[O:21])[N:15]=2)=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[NH3:22].[CH:23](Cl)(Cl)Cl>>[CH3:23][CH2:20][O:19][CH2:18][CH3:14].[NH2:1][C:2]1[C:3]([CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]2[C:18]([NH2:22])=[N:17][S:16](=[O:21])[N:15]=2)=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1

Participants

Reactant 3

HCID 222Ammonia

HCID 6212Chloroform

HCID 159623603-[4-(3-Amino-5-bromopyrid-2-yl)butylamino]-4-methoxy-1,2,5-thiadiazole-1-oxide

Product 1

HCID 86740210Ether 3-[4-(3-amino-5-bromopyrid-2-yl)butylamino]-4-amino-1,2,5-thiadiazole-1-oxide

Procedure

Reaction of 3-[4-(3-amino-5-bromopyrid-2-yl)butylamino]-4-methoxy-1,2,5-thiadiazole-1-oxide (0.56 g) with methanolic ammonia solution (50 ml) at room temperature overnight gave after chromatography on silica in chloroform and trituration with ether 3-[4-(3-amino-5-bromopyrid-2-yl)butylamino]-4-amino-1,2,5-thiadiazole-1-oxide (0.19 g) m.p. 105°-109° C.

Sources & evidence

ORD record: ord-689f2a8f54ed4e7e8d4dd2b72566a17a
Source dataset: uspto-grants-1985_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04532252

Reaction notes

Loading…