Sodium ethoxide → HCID 178457562, compound

HRID 236703Notes

Reaction equation

[C:1]([NH:3][C:4]([NH:9][CH2:10][C:11]#[CH:12])=[N:5][CH2:6][CH2:7][SH:8])#[N:2].[O-]CC.[Na+].[CH3:17][C:18]1[N:19]=[CH:20][NH:21][C:22]=1[CH2:23]Cl>C(O)C.[Cl-].[Na+].O>[C:1]([NH:3][C:4]([NH:5][CH2:6][CH2:7][S:8][CH2:23][C:22]1[NH:21][CH:20]=[N:19][C:18]=1[CH3:17])=[N:9][CH2:10][C:11]#[CH:12])#[N:2]

Participants

Conditions

Temperature: 4 °C

Procedure

A solution of 0.029 g (0.16 m mole) of the product of step A, in 1 ml ethanol containing 0.42 m mole sodium ethoxide, was placed under a nitrogen atmosphere and cooled to 4° C. with stirring. After 5 minutes, 0.035 g (0.21 m mole) of solid 4-methyl-5-chloromethylimidazole was added. The mixture was stirred for 40 minutes, poured into brine (30 ml) and then extracted with chloroform (3×15 ml). After drying (Na2SO4), the solvent was removed by evaporation. The residue was purified by thin layer chromatography on silica gel plates using a methanol-chloroform (1:4) solvent system to give 0.022 g (50%) of the title compound as a syrup which crystallized on standing at room temperature. Trituration with chloroform gave the crystalline product, m.p. 147°-149° C. I.R. (nujol): 3360 (NH), 3300 (C≡CH), 2160 (C≡N), 1600 and 1585 (C=N) cm-1 ; n.m.r. (acetone D6): δ 8.53 (1H, NH), 7.68 (s, 1H), 7.00 (1H, NH), 4.13 (q, 2H, J=2.5 Hz), 3.73 (s, 2H), 3.53 (m, 2H), 2.73 (m, 3H), 2.21 (s, 3H).

Workup

stirringThe mixture was stirred for 40 minutes
extractionextracted with chloroform (3×15 ml)
dry with materialAfter drying (Na2SO4)
customthe solvent was removed by evaporation
customThe residue was purified by thin layer chromatography on silica gel plates

Sources & evidence

ORD record: ord-7282e8213b7f45bb8c123a7e7043e4b0
Source dataset: uspto-grants-1979_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04157340

Reaction notes

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