Trifluoroacetic acid → HCID 178486884, compound

HRID 2228488Notes

Reaction equation

HRID 2228488 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:6][C:3]=1[C:4]#[N:5].[O-:20][C:21]#[N:22].[Na+].FC(F)(F)C(O)=O>ClCCl>[NH2:5][C:4]1[C:3]2[C:2](=[CH:9][C:8]([O:10][CH3:11])=[C:7]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:6]=2)[N:1]=[C:21]([OH:20])[N:22]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 517096Sodium CyanateHCID 110759942-Amino-5-(benzyloxy)-4-methoxybenzonitrile

Product 1

HCID 178486884HCID 178486884, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-amino-5-benzyloxy-4-methoxybenzonitrile (26.7 g, 0.10 mol) in dichloromethane was treated with sodium cyanate (17.1 g, 0.26 mol) and then trifluoroacetic acid (20.9 ml, 0.26 mol) was added dropwise to the resulting mixture at room temperature. After 45 minutes, the mixture was diluted with dichloromethane (11) and stirred for a further 18 hours. The mixture was then concentrated under reduced pressure and partitioned between methanol and 2N aqueous sodium hydroxide and stirred for 2 hours. The methanol was then removed under reduced pressure and the yellow solid isolated by filtration, washing sequentially with water, acetone and diethyl ether to afford the subtitle compound as a yellow solid (18.0 g, 54%). A further quantity of product was obtained by concentration of the filtrate, acidification with concentrated hydrochloric acid (95 ml), warning on a steam bath for 5 minutes, cooling and neutralisation with solid potassium carbonate. The solid obtained was isolated by filtration, washing sequentially with water, ethanol and diethyl ether to afford the subtitle compound as a yellow solid (12.11 g, 93% combined yield). Rf 0.23 (0.880 aqueous ammonia:methanol:dichloromethane 2:14:84, v/v). MS m/z 298 (MH)+.

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. custompartitioned between methanol and 2N aqueous sodium hydroxide
  3. stirringstirred for 2 hours
  4. customThe methanol was then removed under reduced pressure
  5. customthe yellow solid isolated by filtration
  6. washwashing sequentially with water, acetone and diethyl ether

Sources & evidence

ORD record
ord-ddf2f7f5c917492abe29d3a15a9833e4
Source dataset
uspto-grants-2002_07
Patent number
US06417194B1

Reaction notes

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