Hydrochloric Acid → HCID 21388721, compound

HRID 1833310Notes

Reaction equation

HRID 1833310 reaction equation
[CH3:1][CH:2]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:3][NH:4][C:5]1[CH:13]=[C:12]([CH3:14])[C:11]([N+:15]([O-:17])=[O:16])=[CH:10][C:6]=1[C:7](N)=[O:8].Cl.[OH2:31]>>[CH3:1][CH:2]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:3][NH:4][C:5]1[CH:13]=[C:12]([CH3:14])[C:11]([N+:15]([O-:17])=[O:16])=[CH:10][C:6]=1[C:7]([OH:31])=[O:8]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 21388725HCID 21388725, compound

Product 1

HCID 21388721HCID 21388721, compound

Procedure

A mixture of 21.9 grams 2-methyltetradecylamino-4-methyl-5-nitrobenzamide, 60.0 ml water, and 90.0 ml concentrated HCl was heated with stirring at reflux temperature for 16 hours, and then cooled, filtered, washed with water and vacuum dried. The crude product was digested with hot petroleum ether (b.p. = 70-100°), which was cooled and filtered, and the filter cake dried in air overnight. The product was recrystallized from a 3:1 ethanol-water mixture and then recrystallized again from petroleum ether (b.p. 90-100°). Yield = 13.3 grams. m.p. = 98-100°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 16 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. washwashed with water and vacuum
  6. customdried
  7. temperaturewas cooled
  8. filtrationfiltered
  9. customthe filter cake dried in air overnight
  10. customThe product was recrystallized from a 3:1 ethanol-water mixture
  11. customrecrystallized again from petroleum ether (b.p. 90-100°)

Sources & evidence

ORD record
ord-144f2114e2e84b52948b4e6847941097
Source dataset
uspto-grants-1978_01
Patent number
US04066456

Reaction notes

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