Ammonia → HCID 68484085, compound

HRID 1875128Notes

Reaction equation

HRID 1875128 reaction equation
Br[CH2:2][C:3]1[C:4]([Cl:20])=[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([Cl:19])[CH:18]=2)[C:14]#[N:15])[C:6]([F:9])=[CH:7][CH:8]=1.[NH3:21].CO>C(Cl)Cl>[NH2:21][CH2:2][C:3]1[C:4]([Cl:20])=[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([Cl:19])[CH:18]=2)[C:14]#[N:15])[C:6]([F:9])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 684854633-{[3-(Bromomethyl)-2-chloro-6-fluorophenyl]oxy}-5-chlorobenzonitrile

Product 1

HCID 68484085HCID 68484085, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared as described herein using 3-{[3-(bromomethyl)-2-chloro-6-fluorophenyl]oxy}-5-chlorobenzonitrile (728 mg, 1.941 mmol) and NH3 in MeOH (27.7 ml, 194 mmol, 7.0 N) in CH2Cl2 (20 ml) to give the title compound as a white solid (602 mg, 100%) which was used for the next step without purification. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.37-7.43 (1H, m) 7.34 (1H, s) 7.12-7.21 (2H, m) 6.99 (1H, br. s.) 3.98 (2H, br. s.) 1.65-1.89 (2H, m). LCMS: m/z 311 (M+1).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-82e70d7525884b9fa0030465a45dbb3a
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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