Isoamyl Nitrite → Ethyl 2-hydroxyimino-2-(1,2,5-thiadiazol-3-yl)acetate

Reaction equation

[S:1]1[N:5]=[CH:4][C:3]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:2]1.[N:12](OCCC(C)C)=[O:13]>>[OH:13][N:12]=[C:6]([C:3]1[CH:4]=[N:5][S:1][N:2]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

Reactant 2

HCID 8053Isoamyl Nitrite

HCID 12906551Ethyl 2-(1,2,5-thiadiazol-3-yl)acetate

Product 1

HCID 136180295Ethyl 2-hydroxyimino-2-(1,2,5-thiadiazol-3-yl)acetate

Procedure

Ethyl 2-(1,2,5-thiadiazol-3-yl)acetate (9.5 g.) and isopentyl nitrite (10 ml.) were reacted according to a similar manner to that of Example 3(a)(1) to give ethyl 2-hydroxyimino-2-(1,2,5-thiadiazol-3-yl)acetate (a mixture of syn and anti isomers) (10.5 g.), mp 60° to 66° C.

Sources & evidence

ORD record: ord-74846a22f5d843c4b3149f854d228170
Source dataset: uspto-grants-1985_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04544751

Reaction notes

Loading…