Triethylamine → HCID 10028586, compound

HRID 2255255Notes

Reaction equation

HRID 2255255 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH3:14][CH:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]([CH3:25])[CH3:24])[C:18]=1[NH:26][S:27]([CH2:30][C:31]1[N:32]=[N:33][NH:34][N:35]=1)(=[O:29])=[O:28])[CH3:16].CCN(CC)CC>CC#N>[CH3:16][CH:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]([CH3:24])[CH3:25])[C:18]=1[NH:26][S:27]([CH2:30][C:31]1[N:32]=[N:33][N:34]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[N:35]=1)(=[O:29])=[O:28])[CH3:14].[CH3:16][CH:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]([CH3:24])[CH3:25])[C:18]=1[NH:26][S:27]([CH2:30][C:31]1[N:35]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[N:34]=[N:33][N:32]=1)(=[O:29])=[O:28])[CH3:14]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 89191-BromododecaneHCID 19741948HCID 19741948, compound

Product 2

HCID 10028586HCID 10028586, compoundHCID 19741957HCID 19741957, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dodecyl bromide (0.386 g, 1.55 mM) was added dropwise to a solution of N-[2,6-bis(1-methylethyl) phenyl]-2H-tetrazole-5-methanesulfonamide (0.5 g, 1.55 mM), Et3N (0.157 g, 1.55 mM) in CH3CN (50 mL), and heated for 20 hours. The residue from solvent removal was redissolved in 20 mL EtOAc, washed with 0.1 N HCl, brine, and evaporated. N-[2,6-Bis(1-methylethyl) phenyl]-2-dodecyl-2H-tetrazole-5-methanesulfonamide was isolated by chromatography (0.13 g, 22%), mp 85°-86° C., along with trace amounts of N-[2,6-bis(1-methylethyl)phenyl]-1-dodecyl-1H-tetrazole-5-methanesulfonamide.

Workup

  1. temperatureheated for 20 hours
  2. customThe residue from solvent removal
  3. dissolutionwas redissolved in 20 mL EtOAc
  4. washwashed with 0.1 N HCl, brine
  5. customevaporated

Sources & evidence

ORD record
ord-cd72149d618f4078b53e3eea30b53540
Source dataset
uspto-grants-1993_08
Patent number
US05239082

Reaction notes

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