Triethylamine → HCID 18615538, compound

HRID 1265269Notes

Reaction equation

HRID 1265269 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10]Cl)[C:4]=1[OH:12].[CH3:13][N:14]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18][N:17]([CH3:23])[CH2:16][CH2:15]1.[CH2:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])C.[OH-].[Na+]>CO>[CH3:23][N:17]1[CH2:16][CH2:15][N:14]([CH3:13])[CH2:22][CH2:21][N:20]([CH2:2][C:3]2[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][N:17]3[CH2:30][CH2:29][N:26]([CH3:24])[CH2:27][CH2:28][N:14]([CH3:13])[CH2:15][CH2:16]3)[C:4]=2[OH:12])[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 22146Mesitol, alpha(sup 2),alpha(sup 6)-dichloro-HCID 129739721,4-Dimethyl-1,4,7-triazonane

Product 1

HCID 18615538HCID 18615538, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At 0° C., 3.26 g (16 mmol) of 2,6-bischloromethyl4-methylphenol are added in portions to a solution of 5 g (32 mmol) of 1,4-dimethyl-1,4,7-triazacyclononane and 3.21 g (32 mmol) of triethylamine in 150 ml of methanol, and the mixture is stirred for 4 days at room temperature. For work-up, 1.28 g (32 mmol) of sodium hydroxide are added, and the sodium chloride which forms is filtered off. The solvent is removed under reduced pressure and the product is dried for one day under a high vacuum. Yield: 6.1 g (86%). Analysis: 1H-NMR:δ=2.24 (s,3 H, Carom.—CH3); 2.35 (s,12 H, N-CH3); 2.64 (m, 8 H, Carom.—CH2—N—CH2—CH2—N); 2.67 (s, 8 H, H3C—N—CH2—CH2—N—CH3); 2.87 (m, 8 H, Carom.—CH2N—CH2—CH2—N); 3.73 (s, 4 H, Carom.—CH2N); 6.82 (s, 2 H, Carom—H) 13C-NMR: 6=20.4 (Carom.—CH3); 45.4 (N—CH3); 53.0; 55.9; 56.2; (N—CH2—CH2—N); 58.6 (Carom.—CH2—N); 123.0 (Carom.—CH2—N); 127.4 (Carom.—CH3); 130.0 (Carom.—H), 154.7 (Carom.—OH) MS: (electrospray) m/e=447 (M+H⊕, 100%)

Workup

  1. filtrationthe sodium chloride which forms is filtered off
  2. customThe solvent is removed under reduced pressure
  3. customthe product is dried for one day under a high vacuum

Sources & evidence

ORD record
ord-4bfafcc6c9b242ca86244d49678bb76d
Source dataset
uspto-grants-2003_04
Patent number
US06545147B1

Reaction notes

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