1,2-Dimethoxyethane → HCID 53985032, compound

HRID 325573Notes

Reaction equation

HRID 325573 reaction equation
[H-].[Na+].COCCOC.Br[CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:36])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH2:22][CH2:23][CH2:24][CH:25]=[CH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:16]=1.C(N(CC)CC)C>O>[CH2:22]([NH:21][C:17]1[CH:16]=[C:15]([C:14]2[O:36][CH2:10][CH2:11][CH2:12][N:13]=2)[CH:20]=[CH:19][CH:18]=1)[CH2:23][CH2:24][CH:25]=[CH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 8471TriethylamineHCID 24758Sodium hydrideHCID 53902847HCID 53902847, compound

Product 1

HCID 53985032HCID 53985032, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 0.4 g. of sodium hydride in 100 ml. of 1,2-dimethoxyethane is added 2.14 g. of N-(3-bromopropyl)-3-(4-tetradecenylamino)benzamide and 12 ml. of triethylamine. The turbid solution is heated to reflux for 20 hours. The solution is diluted with 100 ml. of water and cooled overnight. The solid is collected, washed with water, crystallized from cyclohexane, and recrystallized from acetonitrile to yield the product.

Workup

  1. temperatureThe turbid solution is heated
  2. temperatureto reflux for 20 hours
  3. additionThe solution is diluted with 100 ml
  4. customThe solid is collected
  5. washwashed with water
  6. customcrystallized from cyclohexane
  7. customrecrystallized from acetonitrile
  8. customto yield the product

Sources & evidence

ORD record
ord-fc6cbd53f8b94036a571121223da5865
Source dataset
uspto-grants-1984_04
Patent number
US04440940

Reaction notes

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