Stannous chloride dihydrate → HCID 118324121, compound

HRID 1778281Notes

Reaction equation

HRID 1778281 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)[C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl>CO.Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:9]2[S:10][CH:11]=[CH:12][N:13]=2)[C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 118324018HCID 118324018, compound

Product 1

HCID 118324121HCID 118324121, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 2-((4-chlorophenyl)(4-nitrophenyl)methyl)thiazole (550 mg, 1.663 mmol, 1 equip) and tin(II) chloride dihydrate (2.321 g, 9.976 mmol, 6 equip) in MeOH (11 mL) and concentrated HCl (1 ml) was heated at reflux temperature until analytical HPLC showed conversion to the desired product. The reaction mixture was made basic with excess triethylamine. The resulting thick precipitate was filtered through CELITE and the filter pad washed thoroughly with methanol. The filtrate was concentrated and the residue was purified by MPLC using ethyl acetate-heptane as the eluent to yield 4-((4-chlorophenyl)(thiazol-2-yl)methyl)aniline as a white solid (250 mg, 50%). (ES, m/z) 301, 303 [M+H]+

Workup

  1. temperatureat reflux temperature until analytical HPLC

Sources & evidence

ORD record
ord-340b7dc0025b485a86f2290e024718e0
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

Loading…