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

HRID 2121386Notes

Reaction equation

HRID 2121386 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]>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 6344DichloromethaneHCID 832214-Iodo-o-toluidineHCID 2724682Lithium diisopropylamideHCID 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:

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-601b0e0bb26d45db8ee0674720462924
Source dataset
uspto-grants-2004_02
Patent number
US06696440B1

Reaction notes

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