Benzhydrylamine → HCID 21714400, compound

HRID 650098Notes

Reaction equation

HRID 650098 reaction equation
[NH2:1][CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.Cl[C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:34][C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][C:36]=1[OH:44]>C1(C)C=CC=CC=1.CN(C=O)C>[C:9]1([CH:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[NH:1][C:23]([NH:34][C:35]2[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][C:36]=2[OH:44])=[O:25])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 7036BenzhydrylamineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 21714400HCID 21714400, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of aminodiphenylmethane (200 mg, 1.09 mmol) in toluene, triethylamine (0.18 ml, 1.11 mmol) and triphosgene (129.4 mg, 0.44 were added. The reaction mixture was stirred at 80° C. for 3 hours. It was cooled to room temperature and all solvent was evaporated. Then 2-amino5-nitrophenol (168 mg, 1.09 mmol) in DMF (2 mL) was added. The reaction mixture was stirred at 80° C. for 16 hours, then cooled to room temperature. Chromatography of the resulting liquid on silica gel (hexane:ethyl acetate; 1:1) gave product (210 mg, 53%). m.p: 237.4-237.9° C.; EI-MS m/z 364 (M+H)+.

Workup

  1. temperatureIt was cooled to room temperature
  2. customall solvent was evaporated
  3. stirringThe reaction mixture was stirred at 80° C. for 16 hours
  4. temperaturecooled to room temperature

Sources & evidence

ORD record
ord-6ceff472a0a74fe089ef9d73bfa83cea
Source dataset
uspto-grants-2001_08
Patent number
US06271261B1

Reaction notes

Loading…