Dimethylamine → HCID 40049759, compound

HRID 2389000Notes

Reaction equation

HRID 2389000 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-5b749852c50a4b6d9010a3ccc447cafe
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

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