Ammonium Hydroxide → 2-Amino-6-[(3-methoxyphenyl)sulfonyl]benzonitrile

HRID 838

Reaction equation

F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)(=[O:12])=[O:11])[C:3]=1[C:4]#[N:5].[NH4+:21].[OH-]>CO.CCO>[NH2:21][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)(=[O:12])=[O:11])[C:3]=1[C:4]#[N:5]

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 0.7 g (2.4 mmol) of 2-fluoro-6-[(3-methoxyphenyl)sulfonyl]benzonitrile (Example 14) in 110 ml of MeOH/EtOH (7:4) was added 20 mL of concentrated NH4OH, This mixture was sealed in a glass-lined bomb and heated at 130° C. for 3 h. After solvent removal, the resultant concentrate was purified by flash column chromatography on silica gel with 5% MeOH in methylene chloride as the eluent. This resulted in 0.16 g (23%) of 2-amino-6-[(3-methoxyphenyl)sulfonyl]benzonitrile as a solid: mp 186°-191° C.; NMR (Me2SO-d6, 200MHz) δ 3.82 (s, 3H), 6.6 (br s, 2H), 7.1 (apparent d, 1H), 7.2-7.7 (m, 6H); mass spec (CI) 289 (M+ +1, 100%). Anal. Calc. for C14H12N2 O3S: C, 58.32; H, 4.20;N, 9.72; S, 11.12. Found: C, 58.13; H, 4.17; N, 9.51; S, 10.95.

Workup

customThis mixture was sealed in a glass-lined bomb
customAfter solvent removal
concentrationthe resultant concentrate
customwas purified by flash column chromatography on silica gel with 5% MeOH in methylene chloride as the eluent
customThis resulted in 0.16 g (23%) of 2-amino-6-[(3-methoxyphenyl)sulfonyl]benzonitrile as a solid

Sources & evidence

ORD record: ord-70d2fe8819214856a573963ea6b87bb1
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05723452

Linked notes

Loading…