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

HRID 840

Reaction equation

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

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 0.73 g (2.7 mmol) of 2-fluoro-6-[(3-methoxyphenyl)sulfinyl]benzonitrile (Example 16) in 65 ml of MeOH/EtOH (2.5:4) 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 0.36 g (53%) of 2-amino-6-[(3-methoxyphenyl)sulfinyl]benzonitrile as a solid: mp 110°-114° C.; NMR. (Me2SO-d6, 200 MHz): δ 3.8 (s, 3H), 6.5 (br s, 2H); 7.1 (apparent d, 1H), 7.0 (apparent d, 2H), 7.2-7.3 (m, 2H), 7.5 (apparent t, 2H); mass spec (CI) 273 (M+ +1, 100%). Anal. Calc. for C14H12N2O2S: C, 61.75; H, 4.44; N, 10.29; S, 11.77. Found: C 61.65; H, 4.46; N, 10.21; S, 11.69.

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 0.36 g (53%) of 2-amino-6-[(3-methoxyphenyl)sulfinyl]benzonitrile as a solid

Sources & evidence

ORD record: ord-efbec65196ea4c25a91fe4f5f0f30b06
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05723452

Linked notes

Loading…