Stearoyl chloride → 2-(1-Methylguanidino)acetic stearic anhydride

HRID 1788318Notes

Reaction equation

HRID 1788318 reaction equation
[C:1](Cl)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH3:21][N:22]([CH2:26][C:27]([O-:29])=[O:28])[C:23]([NH2:25])=[NH:24].[K+]>>[C:1]([O:28][C:27](=[O:29])[CH2:26][N:22]([CH3:21])[C:23]([NH2:25])=[NH:24])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

3

Reactant 2

HCID 8212Stearoyl chloride2×HCID 59641369Potassium 2-(1-methylguanidino)acetate

Product 1

HCID 250059052-(1-Methylguanidino)acetic stearic anhydride

Procedure

Finally, in a dry 2-necked, round bottomed flask, fixed with a separatory funnel, containing 21.27 g (70 mmol) of the prepared stearoyl chloride, and side arm water condenser fixed with a dry receiving flask, is placed 23.40 g (77 mmol) of potassium 2-(1-methylguanidino)acetate. The round bottomed flask is placed in an ice bath and the stearoyl chloride is added drop wise. After addition is completed the mixture is shaken and the ice bath is replaced by a heating mantle. The flask is then heated until no more solution is dropping into the receiving flask. This crude distillate is then further fractionally distilled to yield 2-(1-methylguanidino)acetic stearic anhydride.

Workup

  1. customFinally, in a dry 2-necked, round bottomed flask, fixed with a separatory funnel
  2. customThe round bottomed flask is placed in an ice bath
  3. additionAfter addition
  4. temperatureThe flask is then heated until no more solution
  5. distillationThis crude distillate is then further fractionally distilled

Sources & evidence

ORD record
ord-1980a97a10944bc7b3ebae6466e12b97
Source dataset
uspto-grants-2009_03
Patent number
US07511164B2

Reaction notes

Loading…