Ammonia → HCID 19968568, compound

HRID 975926Notes

Reaction equation

[C:1]([CH:3]1[CH2:12][CH2:11][CH2:10][C:9]2[C:8]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[C:7]([O:18][CH3:19])[CH:6]=[CH:5][C:4]1=2)#[N:2].Cl.[CH2:21](N)[CH2:22][NH2:23].N>CO.CO.C(Cl)(Cl)Cl>[NH:2]1[CH2:21][CH2:22][N:23]=[C:1]1[CH:3]1[CH2:12][CH2:11][CH2:10][C:9]2[C:8]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[C:7]([O:18][CH3:19])[CH:6]=[CH:5][C:4]1=2

Participants

Conditions

Temperature: 0 °C

Procedure

N-(5-Cyano-2-methoxy-5,6,7,8-tetrahydronaphthalen-1-yl)methane-sulfonamide (1.5 g, 5.4 mmol) was dissolved in 200 ml of MeOH and cooled to 0° C. The solution was then treated with dry HCl gas for 2 h, sealed tightly and stored for 12 h at 25° C. The solvent was removed and the residue was redissolved in 100 ml of MeOH, followed by addition of ethylenediamine (0.67 ml, 10 mmol). The resulting solution was stirred at reflux for 12 h. The reaction mixture was concentrated in vacuo, yielding an oily residue which was subjected to column chromatography (25% NH3 sat'd MeOH-CHCl3) to provide 1.3 g (76%) of the desired product. 1H NMR (300 MHz, CD3OD): δ 1.78 (m, 2H), 1.96 (m, 1H), 2.12 (m, 1H), 2.95 (broad t, 2H), 2.98 (s, 3H), 3.82 (s, 3H), 3.90 (broad s, 4H), 4.11 (t, 1H, J=6.3 Hz), 6.96 (t, 1H, J=8.9 Hz), 7.05 (t, 1H, J=8.9 Hz).

Workup

customsealed tightly
customThe solvent was removed
dissolutionthe residue was redissolved in 100 ml of MeOH
temperatureat reflux for 12 h
concentrationThe reaction mixture was concentrated in vacuo
customyielding an oily residue which

Sources & evidence

ORD record: ord-8f8117f16b134e2d88699545cc0cb454
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05610174

Reaction notes

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