Ethanol → HCID 87294509, compound

HRID 872915Notes

Reaction equation

[C:1]([N:20]1[CH:24]=[C:23]([C:25]#[N:26])[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.C(N(CC)CC)C.Cl.[NH2:38][OH:39]>O>[OH:39]/[N:38]=[C:25](/[C:23]1[N:22]=[CH:21][N:20]([C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:24]=1)\[NH2:26]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture containing 1-trityl-1H-imidazole-4-carbonitrile (1.6 g, 4.77 mmol), ethanol (20 ml), triethylamine (1.995 ml, 14.31 mmol) and hydroxylamine hydrochloride (0.663 g, 9.54 mmol) was heated to 70° C. and stirred 4 h. The mixture was cooled with an ice bath, some water (10 ml) was added and the precipitated product filtered and washed well with water. The product was dried with vacuum at 40° C. 1H-NMR (400 MHz; DMSO-d6): δ 5.43-5.50 (m, 2H), 7.01 (d, 1H), 7.04-7.13 (m, 6H), 7.36-7.46 (m, 10H), 9.10 (d, 1H).

Workup

temperatureThe mixture was cooled with an ice bath
filtrationthe precipitated product filtered
washwashed well with water
customThe product was dried with vacuum at 40° C

Sources & evidence

ORD record: ord-3b8f1d093d6e49758f2d8c776460c3de
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975254B2

Reaction notes

Loading…