1,1,1-trimethyl-N-((trimethylsilyl)oxy)silylamine → N5-(3,5-Dichloro-phenyl)-[1,2,4]oxadiazole-3,5-diamine

HRID 1048862Notes

Reaction equation

[C:1](/[N:3]=[C:4](\SC)/[NH:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[CH:7]=1)#[N:2].C[Si](C)(C)[NH:18][O:19][Si](C)(C)C>C(Cl)(Cl)(Cl)Cl>[Cl:12][C:10]1[CH:11]=[C:6]([NH:5][C:4]2[O:19][N:18]=[C:1]([NH2:2])[N:3]=2)[CH:7]=[C:8]([Cl:13])[CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

In a 5 mL microwave vial, (Z)-methyl N′-cyano-N-(3,5-dichlorophenyl)carbamimidothioate (156 mg, 0.6 mmol, Eq: 1.00) and N,O-bis(trimethylsilyl)hydroxylamine (160 mg, 900 μmol, Eq: 1.5) were combined with CCl4 (1 ml) to give a colorless suspension which was capped and heated in a 80° C. oil bath for 2.5 hr. The mixture was concentrated in vacuo and MeOH added. The mixture was stirred at RT for 18 hours. The reaction mixture was concentrated in vacuo and the crude material was purified by preparative TLC (silica gel, 1.0 mm, 9:1 DCM/MeOH) to give product which was recrystallized from MeOH and dried in vacuo (89° C., 2 torr, overnight) to give 32 mg (22%) of desired product as a light brown solid.

Workup

customto give a colorless suspension which
customwas capped
concentrationThe mixture was concentrated in vacuo and MeOH
additionadded
concentrationThe reaction mixture was concentrated in vacuo
customthe crude material was purified by preparative TLC (silica gel, 1.0 mm, 9:1 DCM/MeOH)
customto give product which
customwas recrystallized from MeOH
customdried in vacuo (89° C., 2 torr, overnight)

Sources & evidence

ORD record: ord-f56b8cd1cb0c4c449ffb382609d13e6d
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382218B2

Reaction notes

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