Dodecylamine → HCID 14646906, compound

HRID 981352Notes

Reaction equation

HRID 981352 reaction equation
[CH2:1]([NH2:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Br:14][CH:15]1[CH2:20][C:19](=[O:21])[O:18][C:16]1=[O:17]>CCCCCC>[Br:14][CH:15]([CH2:20][C:19]([NH:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:21])[C:16]([OH:18])=[O:17]

Participants

4

Reactant 2

HCID 13583DodecylamineHCID 2304012-Bromosuccinic anhydride

Product 1

HCID 14646906HCID 14646906, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent3×

Procedure

A solution of 9.3 g. (0.05 mole) of dodecylamine in 30 ml. of hexane is added dropwise to a stirred mixture of 9.0 g. (0.05 mole) of 2-bromosuccinic anhydride in 70 ml. of hexane at 5°-10° C. over a period of 15 minutes. Reaction is exothermic and the mixture is stirred for an additional 15 minutes while still in cooling bath. As a result, the temperature rises to 15° C. and the reaction takes the appearance of a white emulsion. Hexane (100 ml.) is added and stirring is continued at ambient temperature for 24 hours. The white insoluble solid is filtered off, washed several times with hexane then dried at about 50° C. and reduced pressure to obtain 16.1 g. (89% yield) of a white slightly waxy solid product of this example; m. p. 62°-70° C. (opaque).

Workup

  1. customReaction
  2. temperaturein cooling bath
  3. customrises to 15° C.
  4. stirringstirring
  5. waitis continued at ambient temperature for 24 hours
  6. filtrationThe white insoluble solid is filtered off
  7. washwashed several times with hexane
  8. customthen dried at about 50° C.
  9. customreduced pressure to obtain 16.1 g

Sources & evidence

ORD record
ord-1ef0b3f0b1c74edf93f5542b9f2d9ee6
Source dataset
uspto-grants-1991_02
Patent number
US04990652

Reaction notes

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