Formamide → N-(1,3,4,9-tetrahydro-2H-carbazol-2-yl)formamide

HRID 66790Notes

Reaction equation

HRID 66790 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][CH:2]1[NH2:14].[CH:15](N)=[O:16]>O>[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][CH:2]1[NH:14][CH:15]=[O:16]

Participants

4

Reactant 2

HCID 713FormamideHCID 205292292,3,4,9-Tetrahydro-1H-carbazol-2-amine

Product 1

HCID 20529254N-(1,3,4,9-tetrahydro-2H-carbazol-2-yl)formamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8.90 g (0.048 mol) of 2,3,4,9-tetrahydro-1H-carbazol-2-amine and 65 ml of dry formamide was stirred and heated under N2 for 5 hr at 95°-100° C. The cooled reaction mixture was poured into H2O, and the precipitated gum extracted with CHCl3. The combined extracts were washed with 0.1 N HCl, 5% aqueous NaHCO3, and H2O, and dried. Et2O-trituration of the residue remaining after evaporation of the CHCl3 gave a tan solid, 8.58 g, mp 123°-126°. For analysis, it was necessary to dry the recrystallized (EtOH) sample at 120° (P2O5, 0.02 mm, 20 hr), mp 169°-171°.

Workup

  1. temperatureheated under N2 for 5 hr at 95°-100° C
  2. customThe cooled reaction mixture
  3. extractionthe precipitated gum extracted with CHCl3
  4. washThe combined extracts were washed with 0.1 N HCl, 5% aqueous NaHCO3, and H2O
  5. customdried
  6. customafter evaporation of the CHCl3
  7. customgave a tan solid, 8.58 g, mp 123°-126°
  8. customto dry the
  9. customrecrystallized (EtOH) sample at 120° (P2O5, 0.02 mm, 20 hr), mp 169°-171°

Sources & evidence

ORD record
ord-a66a51a909944e09b6a14c438d190aad
Source dataset
uspto-grants-1982_08
Patent number
US04343812

Reaction notes

Loading…