Cesium carbonate → HCID 86653109, compound

HRID 1258548Notes

Reaction equation

HRID 1258548 reaction equation
[OH:1][N:2]=[C:3]([C:10]1[N:14]([CH3:15])[N:13]=[N:12][N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Cl:22][C:23]1[S:24][C:25]([Cl:30])=[C:26]([CH2:28]Cl)[N:27]=1>CC#N>[Cl:22][C:23]1[S:24][C:25]([Cl:30])=[C:26]([CH2:28][O:1][N:2]=[C:3]([C:10]2[N:14]([CH3:15])[N:13]=[N:12][N:11]=2)[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:27]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 14338691HCID 14338691, compoundHCID 135990939N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

Product 1

HCID 86653109HCID 86653109, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (2.15 g, 10.58 mmol, 1.0 eq.) in 20 ml of MeCN was added Cs2CO3 (4.12 g, 12.69 mmol, 1.2 eq.) followed by KI (0.17 g, 1.05 mmol, 0.1 eq.) in one portion. The resulting suspension was stirred for 5 mins before addition of 2,5-dichloro-4-(chloromethyl)-1,3-thiazole (2.35 g, 11.63 mmol, 1.1 eq.) in one portion. The reaction was stirred for 24 hrs at room temperature. The solvent was evaporated and the residue was dissolved in EtOAc and washed with H2O. The organic layer was separated, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel to give N-[(2,5-dichloro-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (1.65 g, 42% yield, 86:14 mixture of stereoisomers) as a yellow viscous oil.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with H2O
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-36271fd3144b4a33a92afd6ed758c671
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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