Ammonia → 2-Amino-4-iodobenzamide

HRID 1424415Notes

Reaction equation

HRID 1424415 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].CC[N:14]=C=NCCCN(C)C.ON1C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.N>CN(C=O)C.O>[NH2:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:14])=[O:5]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 227247802-Amino-4-iodo-benzoic acid

Product 1

HCID 666116532-Amino-4-iodobenzamideYield 52.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-4-iodobenzoic acid (2.5 g, 9.50 mmol) in DMF (10 mL) at rt under argon were added EDCI (2.18 g, 11.40 mmol), 1-hydroxybenzotriazole (1.54 g, 11.40 mmol), DIEA (1.98 mL, 11.40 mmol), and ammonia (7.0 N solution in MeOH, 1.90 mL, 13.30 mmol). The dark solution was stirred at rt overnight and diluted with H2O until precipitate formed. The precipitate was separated by filtration, washed with H2O, and dried under high vacuum for several hours to afford 2-amino-4-iodobenzamide as a tan solid (1.3 g, 52%). LC-MS (ESI) m/z 263 (M+H)+.

Workup

  1. customformed
  2. customThe precipitate was separated by filtration
  3. washwashed with H2O
  4. customdried under high vacuum for several hours

Sources & evidence

ORD record
ord-dab2074cb37247089757b2cf1dced197
Source dataset
uspto-grants-2015_01
Patent number
US08927711B2

Reaction notes

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