Dimethylamine → HCID 40049759, compound

HRID 1865663Notes

Reaction equation

HRID 1865663 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4](O)=[O:5].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:23]2[N:24]=[CH:25]C=CC=2N=N1.C(N(CC)CC)C.CNC>ClCCl>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([N:24]([CH3:25])[CH3:23])=[O:5]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 72911Benzoic acid, 2-amino-5-iodo-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 40049759HCID 40049759, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-5-iodobenzoic acid (5.0 g, 19 mmol) was dissolved in dichloromethane (100 mL). O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (7.9 g, 21 mmol) and triethyl amine (2.1 g, 21 mmol) were added with magnetic stirring. After 5 min., dimethyl amine (2 N in THF, 19 mL, 38 mmol) was added and the resulting solution was stirred overnight. The reaction solution was washed with aqueous saturated sodium chloride and concentrated. The residue was purified by flash chromatography on silica gel using a gradient of methanol in dichloromethane to afford 2-amino-5-iodo-N,N-dimethyl-benzamide (5.4 g, 98% yield) as yellow solids. MS: m/z 291 (M+H+).

Workup

  1. washThe reaction solution was washed with aqueous saturated sodium chloride
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography on silica gel using a gradient of methanol in dichloromethane

Sources & evidence

ORD record
ord-db50ff3089a14b5489268465bba47544
Source dataset
uspto-grants-2009_12
Patent number
US07626021B2

Reaction notes

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