Ammonia → HCID 22476045, compound

HRID 378324Notes

Reaction equation

HRID 378324 reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[I:11].[NH3:12].CO.C(Cl)[Cl:16]>CO.C1COCC1>[ClH:16].[NH2:12][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[I:11]

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 887MethanolHCID 6344DichloromethaneHCID 224760954-(Bromomethyl)-3-iodobenzonitrile

Product 1

HCID 22476045HCID 22476045, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

12.1 g (37.6 mmol) of 4-bromomethyl-3-iodobenzonitrile in 200 ml of MeOH/THF 1:1 were slowly added dropwise to 200 ml of conc. ammonia solution/MeOH (saturated with NH3) 1:1, simultaneously passing NH3 into the reaction mixture. The temperature was maintained at 50° C. After 4 h, the solvent was stripped off, and the product was taken up in DCM, dried and precipitated with ethereal HCl. 8.6 g of 4-aminomethyl-3-iodobenzonitrile hydrochloride were obtained. 1H-NMR (DMSO-d6, δ in ppm): 8.8 (broad signal, NH3+), 8.43 (1H), 7.98 (1H), 7.70 (1H), 4.13 (2H)

Workup

  1. customdried
  2. customprecipitated with ethereal HCl

Sources & evidence

ORD record
ord-fcf9f33c0454464f9d9cc2e10e711601
Source dataset
uspto-grants-2000_02
Patent number
US06030972

Reaction notes

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