Sodium Hydroxide → HCID 20503643, compound

HRID 850992Notes

Reaction equation

HRID 850992 reaction equation
C(OC([N:8]([C:25]1[CH:26]=[C:27]([C:30](N2C=CN=C2)=[O:31])[S:28][CH:29]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=O)(C)(C)C.[OH-].[Na+].[NH2:39][CH2:40][CH:41]([OH:44])[CH2:42][OH:43]>C(Cl)(Cl)Cl>[OH:44][CH:41]([CH2:42][OH:43])[CH2:40][NH:39][C:30]([C:27]1[S:28][CH:29]=[C:25]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:26]=1)=[O:31]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 735613-Amino-1,2-propanediolHCID 20503658HCID 20503658, compound

Product 1

HCID 20503643HCID 20503643, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture containing 4.1 g. of 1-{4-[N-(tert-butyloxycarbonyl)-N-(hexadecyl)amino]-2-thiophenecarbonyl}imidazole, 50 ml. of chloroform, and 50 ml. of 5 N sodium hydroxide is added 1.1 g. of 3-amino-1,2-propanediol. The solution is vigorously stirred for 24 hours, the layers are separated, and the chloroform solution is washed once with 50 ml. of 1 N sodium hydroxide. The solvent is evaporated and the residue is heated for 30 minutes at 40° C. in 50 ml. of anhydrous trifluoroacetic acid. The solvent is again evaporated and the oil is crystallized from acetone to yield light yellow crystals of N-(2,3-dihydroxypropyl)-4-hexadecylamino-2-thiophenecarboxamide.

Workup

  1. additionTo a mixture containing 4.1 g
  2. customthe layers are separated
  3. washthe chloroform solution is washed once with 50 ml
  4. customThe solvent is evaporated
  5. customThe solvent is again evaporated
  6. customthe oil is crystallized from acetone

Sources & evidence

ORD record
ord-1437eeb5baee451ab2db5920b3824d5a
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

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