Hydrochloric Acid → HCID 70547027, compound

HRID 67790Notes

Reaction equation

HRID 67790 reaction equation
Cl[NH:2][C:3](=O)[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]C.[NH:20]([CH2:22]C(O)=O)[CH3:21].[OH-:26].[Na+].Cl.[C:29]([OH:33])(C)(C)[CH3:30]>O>[CH3:21][N:20]1[CH2:30][C:29](=[O:33])[N: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][CH3:17])[C:22]1=[O:26]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1088SarcosineHCID 6386tert-ButanolHCID 14798Sodium HydroxideHCID 19040091HCID 19040091, compound

Product 1

HCID 70547027HCID 70547027, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture containing 57.9 g (0.2 mol) of palmitic N-chloramide dissolved in 500 ml tertiary butanol at 40° C. was added 17.8 g (0.2 mol) sarcosine, 16 g (0.4 mol) sodium hydroxide and 100 ml of water. The resulting mixture was heated at 50° C. for 1 hour and then acidified with 10% hydrochloric acid (pH 3) without cooling and tertiary butanol is distilled off. During distillation, the N-methyl-N'-n-pentadecyl ureidoacetic acid precipitated was first converted into 1-methyl-3-n-pentadecyl hydantoin with splitting off of water. The initially oily hydantoin crystallized out from the aqueous distillation residue to yield 59 g (91% yield) 1-methyl-3-n-pentadecyl hydantoin of the formula ##STR9## having a melting point of 58°-60° C. and the following analysis:

Workup

  1. temperaturewithout cooling
  2. distillationtertiary butanol is distilled off
  3. distillationDuring distillation
  4. customthe N-methyl-N'-n-pentadecyl ureidoacetic acid precipitated
  5. customThe initially oily hydantoin crystallized out from the aqueous distillation residue

Sources & evidence

ORD record
ord-62b5df7c3f62446da712da0fa0b82f95
Source dataset
uspto-grants-1982_08
Patent number
US04346233

Reaction notes

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