Ammonia → Selenazofurin

HRID 2291147Notes

Reaction equation

HRID 2291147 reaction equation
[C@@H:1]1([C:10]2[Se:11][CH:12]=[C:13]([C:15]([O:17]C)=O)[N:14]=2)[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@H:2]1[OH:3].[NH3:19].ClCCl.CO>CO>[C@@H:1]1([C:10]2[Se:11][CH:12]=[C:13]([C:15]([NH2:19])=[O:17])[N:14]=2)[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@H:2]1[OH:3]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 13728682HCID 13728682, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 100665Selenazofurin

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 168 g (521 mmol) of the methyl ester, VI, in 2.0 l of methanol was cooled to approximately 10° and treated with anhydrous ammonia gas for eight hours. The solution was allowed to stand at room temperature overnight. The TLC (SiO2, dichloromethane-methanol, 5:1) indicated complete conversion to the desired product. A very small amount of a red solid was removed by filtration. The filtrate was evaporated under reduced pressure and the residue was recrystallized from 2-propanol and dried at 40° under 0.5 atmospheres to give 136 g (84.9%) of the product, mp 128-130 (lit. (see below) mp 131°-133°).

Sources & evidence

ORD record
ord-bcdb4de816c841e4ab1bf15a9429199e
Source dataset
uspto-grants-1986_10
Patent number
US04619996

Reaction notes

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