2-Oxopropanethioamide → 7'-Bromo-5''-methyl-3',4'-dihydrodispiro[cyclopropane-1,2'-naphthalene-1',2''-imidazole]-4''(3''H)-thione

HRID 1468230Notes

Reaction equation

HRID 1468230 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8]3([CH2:14][CH2:13]3)[C:9]2=[NH:12])=[CH:4][CH:3]=1.O=[C:16]([CH3:20])[C:17](=[S:19])[NH2:18]>CO>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8]3([C:9]42[NH:18][C:17](=[S:19])[C:16]([CH3:20])=[N:12]4)[CH2:14][CH2:13]3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 207652372-OxopropanethioamideHCID 867067067'-Bromo-3',4'-dihydro-1'H-spiro[cyclopropane-1,2'-naphthalen]-1'-imine2×

Product 1

HCID 867067077'-Bromo-5''-methyl-3',4'-dihydrodispiro[cyclopropane-1,2'-naphthalene-1',2''-imidazole]-4''(3''H)-thioneYield 71.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

7′-Bromo-3′,4′-dihydro-1′H-spiro[cyclopropane-1,2′-naphthalen]-1′-imine (Intermediate 11, 717 mg, 2.87 mmol) and 2-oxopropanethioamide (970 mg, 9.40 mmol) were dissolved in dry MeOH (25 mL) and heated at 60° C. under argon for 24 h. After standing at r.t. overnight the formed precipitate was filtered and washed with MeOH. Drying in vacuo afforded the title compound (688 mg, 65% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.27-0.35 (m, 1 H), 0.35-0.45 (m, 2 H), 0.47-0.53 (m, 1 H), 1.69-1.79 (m, 1 H), 2.03-2.12 (m, 1 H), 2.27 (s, 3 H), 2.90 (t, 2 H), 6.73 (d, 1 H), 7.24 (d, 1 H), 7.47 (dd, 1 H), 12.28 (s, 1 H); MS (ES+) m/z 335.0 [M+H]+.

Workup

  1. filtrationthe formed precipitate was filtered
  2. washwashed with MeOH
  3. customDrying in vacuo

Sources & evidence

ORD record
ord-99fb715f305f4eab98e8eacd430b0254
Source dataset
uspto-grants-2015_04
Patent number
US09000184B2

Reaction notes

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