Potassium Carbonate → HCID 67234995, compound

HRID 339151Notes

Reaction equation

HRID 339151 reaction equation
[C:1]1([N:7]2[C:11]([SH:12])=[N:10][N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]1([N:7]2[C:11]([S:12][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])=[N:10][N:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13789512-Bromo-1-dodecanolHCID 1785279861-phenyltetrazole-5-thiol

Product 1

HCID 67234995HCID 67234995, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Phenyl-1H-tetrazole-5-thiol, 12-bromododecan-1-ol and anhydrous potassium carbonate were mixed together in acetone for 18 hrs at room temperature to provide 12-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-dodecan-1-ol in 77% yield following work up and recrystallisation. Ammonium molybdate (VI) tetrahydrate in 35% H2O2 were added to a stirred solution of the solid in THF IMS (500 ml) at 10° C. and stirred at room temperature for 20 hrs. Work-up and crystallisation gave a white solid (m.p.: 56-58° C.), 12-(1-phenyl-1H-tetrazol-5-sulfonyl)-dodecan-1-ol in 95% yield. N-Bromosuccinimide was added to a solution of the alcohol and triphenylphosphine in dichloromethane and the reaction stirred at room temperature for 75 min. Work-up and purification by chromatography provided a white solid (m.p.: 63-65° C.), 5-(12-bromo-dodecane-1-sulfonyl)-1-phenyl-1H-tetrazole in 72% yield.

Sources & evidence

ORD record
ord-4fde77b1a7f646c4aa2a80d2773f6960
Source dataset
uspto-grants-2014_11
Patent number
US08889894B2

Reaction notes

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