Triethylamine → HCID 20081998, compound

HRID 1609580Notes

Reaction equation

HRID 1609580 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:12][CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.C(N(CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C)C=O>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([NH:12][CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)=[O:6]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 310183-PyridinemethanamineHCID 798582-Amino-5-bromobenzoic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 20081998HCID 20081998, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 238 ml of dimethylformamide were dissolved 23.8 g of 2-amino-5-bromobenzoic acid, 13.1 g of 3-aminomethylpyridine and 24.5 g of triethylamine, and the solution was chilled with ice. To this solution was dropwise added 33.3 g of diphenylphosphoryl azide in 10 minutes, and the resultant mixture was stirred at room temperature for 18 hours. The reaction mixture was poured onto ice water. The precipitated solid was filtered, washed with water and dried to give 29.4 g of the titled compound.

Workup

  1. temperaturethe solution was chilled with ice
  2. customin 10 minutes
  3. additionThe reaction mixture was poured onto ice water
  4. filtrationThe precipitated solid was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-0cb6d385522d4ee98fa20e8209bffa4d
Source dataset
uspto-grants-1995_03
Patent number
US05401756

Reaction notes

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