4-Iodo-o-toluidine → 4-Chloro-2-(1H-tetrazol-5-yl)-(4-iodo-2-methyl-phenyl)-amine

HRID 1744905Notes

Reaction equation

HRID 1744905 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[Li+].CC([N-]C(C)C)C.[NH:18]1[C:22](C2C=C(Cl)C=CC=2F)=[N:21][N:20]=[N:19]1.C(Cl)[Cl:32].CO>C1COCC1>[Cl:32][C:7]1([I:9])[CH:6]=[CH:5][CH:3]([NH2:4])[C:2]([C:22]2[NH:21][N:20]=[N:19][N:18]=2)([CH3:1])[CH2:8]1

Participants

6

Reactant 4

HCID 832214-Iodo-o-toluidineHCID 2724682Lithium diisopropylamideHCID 21226129Dichloromethane methanolHCID 178505771HCID 178505771, compound

Product 1

HCID 1784216814-Chloro-2-(1H-tetrazol-5-yl)-(4-iodo-2-methyl-phenyl)-amineYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-methyl-4-iodoaniline (3.52 g, 0.0151 mol) in THF (25 mL) at −78° C., LDA (2 molar solution in THF, 11.33 mL, 0.02267 mol) was added dropwise. After stirring for 0.5 hours, a solution of 1-(tetrazol-5-yl)-2-fluoro-5-chlorobenzene (1.5 g, 0.00756 mol) in THF (15 mL) was added dropwise. The reaction was stirred for 16 hours as it warmed up to room temperature. The reaction mixture was quenched with aqueous conc. NH4Cl solution and extracted with CH2Cl2. The organic layer was dried (MgSO4) and the solvent removed giving a crude product as an oil. The oil with CH2Cl2->CH2Cl2:MeOH (9.7:0.3) gave 1.5 g (48%) of the desired product: mp 205-208;

Workup

  1. stirringThe reaction was stirred for 16 hours as it
  2. customThe reaction mixture was quenched with aqueous conc. NH4Cl solution
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvent removed
  6. customgiving a crude product as an oil

Sources & evidence

ORD record
ord-31eca280af42457f8d6032fb195a6226
Source dataset
uspto-grants-2006_03
Patent number
US07019033B2

Reaction notes

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