Methylamine → HCID 178485192, compound

HRID 2357552Notes

Reaction equation

HRID 2357552 reaction equation
[CH3:1][NH2:2].[Cl:3][C:4]1[CH:13]=[CH:12][C:7]([C:8](=[N:10][OH:11])Cl)=[C:6]([F:14])[C:5]=1[I:15]>C1COCC1>[Cl:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([NH:2][CH3:1])=[N:10][OH:11])=[C:6]([F:14])[C:5]=1[I:15]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86607608HCID 86607608, compound

Product 1

HCID 178485192HCID 178485192, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylamine (33% wt solution in absolute ethanol, 1.9 mL, 18 mmol) was added dropwise to a solution of 4-chloro-2-fluoro-3-iodobenzoyl chloride oxime (0.600 g, 1.8 mmol) in anhydrous THF (10 mL) at 0° C. The reaction mixture was stirred at RT for 1 h. The volatile solvents were removed under reduced pressure. Flash chromatography on silica gel (dichloromethane:hexane 25:75) gave 4-chloro-2-fluoro-N′-hydroxy-3-iodo-N-methylbenzamidine as an amorphous white solid. MS (ESI, pos.ion) m/z: 330.9 (M+1)

Workup

  1. customThe volatile solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-349dcf954d1d4474a663e212c1670c0f
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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