Sodium Hydroxide → 2-Carbamyl-4-hexadecylaminothiophene

HRID 850961Notes

Reaction equation

HRID 850961 reaction equation
[CH2:1]([NH:17][C:18]1[CH:19]=[C:20]([C:23]#[N:24])[S:21][CH:22]=1)[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][CH3:16].[OH-:25].[Na+]>COCCO>[C:23]([C:20]1[S:21][CH:22]=[C:18]([NH:17][CH2:1][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][CH3:16])[CH:19]=1)(=[O:25])[NH2:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131349914-Hexadecylamino-2-cyanothiophene

Product 1

HCID 131349932-Carbamyl-4-hexadecylaminothiophene

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 6.9 g. of 4-hexadecylamino-2-cyanothiophene, 80 ml. of methyl cellosolve, and 80 ml. of 1 N sodium hydroxide is refluxed for 21 hours. After cooling in an ice bath, the solid is filtered and thoroughly washed with methylene chloride. The solid is then added to 100 ml. of water and 5 ml. of concentrated hydrochloric acid and stirred for 8 hours. The solid is filtered and recrystallized from isopropanol.

Workup

  1. additionA mixture of 6.9 g
  2. temperatureAfter cooling in an ice bath
  3. filtrationthe solid is filtered
  4. washthoroughly washed with methylene chloride
  5. additionThe solid is then added to 100 ml
  6. filtrationThe solid is filtered
  7. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-b644d3a0e3614ba791118f70976f2154
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

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