Hydrochloric Acid → HCID 21469524, compound

HRID 1756986Notes

Reaction equation

HRID 1756986 reaction equation
C(C1NC=CN=1)(C1NC=CN=1)=O.[CH2:13]([C:26]1[S:27][CH:28]=[C:29]([CH2:31][C:32]([OH:34])=O)[N:30]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].[CH3:35][O:36][C:37]1[CH:43]=[C:42]([O:44][CH3:45])[CH:41]=[C:40]([O:46][CH3:47])[C:38]=1[NH2:39].Cl.C(N(CC)CC)C>C1COCC1>[CH2:13]([C:26]1[S:27][CH:28]=[C:29]([CH2:31][C:32]([NH:39][C:38]2[C:40]([O:46][CH3:47])=[CH:41][C:42]([O:44][CH3:45])=[CH:43][C:37]=2[O:36][CH3:35])=[O:34])[N:30]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 842712,4,6-Trimethoxyaniline2×HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 21469482HCID 21469482, compound

Product 1

HCID 21469524HCID 21469524, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Carbonyl dimidazole (0.38 g, 2.35 mmol) was added to a solution of 2-tridecyl-4-thiazole acetic acid (0.71 g, 2.28 mmol) in dry THF (50 mL), and the resulting mixture was stirred at room temperature for 1.5 hours, then 2,4,6-trimethoxyaniline made in situ [2,4,6-trimethoxyaniline.HCl (0.05 g, 2.28 mmol) and triethylamine (0.32 mL, 2.28 mmol) were stirred together at room temperature for 0.5 hour] was added and the solution stirred for 3 days at room temperature, then filtered, and the filtrate stirred with 3:1 chloroform/water (200 mL) for 1 hour. The organic layer was separated, washed with brine, dried over Na2SO4, filtered, concentrated, and triturated with hexanes to yield a grey solid (0.93 g, 82%) which was air dried.

Workup

  1. additionwas added
  2. stirringthe solution stirred for 3 days at room temperature
  3. filtrationfiltered
  4. stirringthe filtrate stirred with 3:1 chloroform/water (200 mL) for 1 hour
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customtriturated with hexanes

Sources & evidence

ORD record
ord-af9a62b6bb474f1b855204fc9815e216
Source dataset
uspto-grants-1995_08
Patent number
US05441975

Reaction notes

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