1,2-Dimethoxyethane → HCID 54314085, compound

HRID 904503Notes

Reaction equation

HRID 904503 reaction equation
Br.Br[CH2:3][CH2:4][NH2:5].COCCOC.Cl.[CH2:13]([NH:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1)[CH2:14][CH2:15][CH:16]=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[CH2:13]([NH:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]2[O:33][CH2:3][CH2:4][N:5]=2)=[CH:30][CH:29]=1)[CH2:14][CH2:15][CH:16]=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 3

HCID 80711,2-Dimethoxyethane2×HCID 27742172-Bromoethylamine hydrobromideHCID 73746988HCID 73746988, compound

Product 1

HCID 54314085HCID 54314085, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolvent

Procedure

To a slurry of 15 g. of 2-bromoethylamine hydrobromide in 150 ml. of 1,2-dimethoxyethane are added simultaneously solutions of 31 g. of 4-(4-tetradecenylamino)benzoyl chloride hydrochloride in 60 ml. of 1,2-dimethoxyethane and 50 cc. of triethylamine (dropwise). Upon addition of 0.5 g. of 4-dimethylaminopyridine the mixture is stirred at room temperature overnight. The solution is refluxed for one hour and filtered. The solid is oven dried and partitioned between methylene chloride and water. The layers are separated and the organic phase dried over magnesium sulfate. The organic layer is concentrated and the residue collected and crystallized from cyclohexane and recrystallized from acetonitrile to yield the product.

Workup

  1. additionUpon addition of 0.5 g
  2. temperatureThe solution is refluxed for one hour
  3. filtrationfiltered
  4. customdried
  5. custompartitioned between methylene chloride and water
  6. customThe layers are separated
  7. dry with materialthe organic phase dried over magnesium sulfate
  8. concentrationThe organic layer is concentrated
  9. customthe residue collected
  10. customcrystallized from cyclohexane
  11. customrecrystallized from acetonitrile
  12. customto yield the product

Sources & evidence

ORD record
ord-57086d25b6e749129e1cbdef183685d6
Source dataset
uspto-grants-1980_10
Patent number
US04230878

Reaction notes

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