Methanol → HCID 58424504, compound

HRID 2096515Notes

Reaction equation

HRID 2096515 reaction equation
Cl.[CH3:2][NH:3][OH:4].CO[Na].[Br:8][C:9]1[CH:10]=[C:11]2C(=[CH:17][CH:18]=1)O[CH2:14][CH2:13][C:12]2=[N:19][C:20]#[N:21].[CH3:22][OH:23]>>[Br:8][C:9]1[CH:10]=[C:11]2[C:12]3([O:4][N:3]([CH3:2])[C:20]([NH2:21])=[N:19]3)[CH2:13][CH2:14][O:23][C:22]2=[CH:17][CH:18]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 77906N-methylhydroxylamine hydrochlorideHCID 58424110N-(6-bromochroman-4-ylidene)cyanamideHCID 178418582HCID 178418582, compound

Product 1

HCID 58424504HCID 58424504, compoundYield 88%

Procedure

To a solution of N-methyl-hydroxylamine hydrochloride (101 mg, 1.2 mmol) in MeOH (4 mL) was added MeONa (0.24 mL, 25% (Wt.) in MeOH), followed by N-(6-bromochroman-4-ylidene)cyanamide (300 mg, 1.2 mmol). After stirring for 10 minutes, the solvent was removed in vacuo. The resulting residue was purified by preparative TLC to give 6-bromo-2′-methyl-2′H-spiro[chroman-4,5′-[1,2,4]oxadiazol]-3′-amine (315 mg, 88%).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe resulting residue was purified by preparative TLC

Sources & evidence

ORD record
ord-40714242ca45453d8a0210cda8b2bd2d
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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