1-Pentanethiol → HCID 86653124, compound

HRID 1258568Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([CH2:8][O:9][N:10]=[C:11]([C:18]2[N:22]([CH3:23])[N:21]=[N:20][N:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[CH:4][CH:3]=1.[CH2:24]([SH:29])[CH2:25][CH2:26][CH2:27][CH3:28].C([O-])([O-])=O.[Cs+].[Cs+].C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>CN1C(=O)CCC1>[CH3:23][N:22]1[C:18]([C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:10][O:9][CH2:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([S:29][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[N:7]=2)=[N:19][N:20]=[N:21]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of N-[(6-bromopyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.3 g, 0.80 mmol, 1 eq.) in 2 ml of NMP were added 1-pentanethiol (0.084 g, 0.80 mmol, 1 eq.), Cs2CO3 (0.262 g, 0.80 mmol, 1 eq.). The reaction was microwaved (30 sec prestirring, abs-normal, fixed-hold) 120° C. for 60 s. Then a mixture water/EtOAc (1/1) was added and the aqueous layer was separated and extracted with EtOAc. The organics were combined, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel to give 1-(1-methyl-1H-tetrazol-5-yl)-N-{[6-(pentylsulfanyl)pyridin-2-yl]methoxy}-1-phenylmethanimine (0.058 g, 17% yield) as a viscous oil.

Workup

customThe reaction was microwaved
customthe aqueous layer was separated
extractionextracted with EtOAc
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-d38a4f9c34404545bb939b005f1abd41
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466176B2

Reaction notes

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