Ammonia → 6-Bromo-5'-methylspiro[chromane-4,2'-imidazol]-4'-amine

HRID 1965027Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([N:15]=[C:14]([CH3:16])[C:13](=S)[NH:12]3)[CH2:10][CH2:9][O:8][C:5]2=[CH:6][CH:7]=1.[NH3:18]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([N:12]=[C:13]([NH2:18])[C:14]([CH3:16])=[N:15]3)[CH2:10][CH2:9][O:8][C:5]2=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

6-Bromo-4′-methylspiro[chroman-4,2′-imidazole]-5′(1′H)-thione (0.10 g, 0.32 mmol, Intermediate 3) was dissolved in MeOH (1 mL) and 7M ammonia in MeOH (4 mL, 28 mmol) was added. The solution was heated at 60° C. for 12 h in a sealed vial. The solution was evaporated in vacuo. The treatment with 7M ammonia was repeated in the same way one more time. Evaporation in vacuo gave the title compound (73 mg, 77% yield) which was used without further purification in the following step. 1H NMR (400 MHz, CDCl3) δ ppm 2.11 (m, 2 H), 2.35 (s, 3 H), 4.53 (m, 2 H), 4.98 (br s, 2 H), 6.66 (m, 1 H), 6.78 (d, 1 H), 7.22 (m, 1 H); MS (ES+) m/z 294 [M+H]+.

Workup

customThe solution was evaporated in vacuo
customEvaporation in vacuo

Sources & evidence

ORD record: ord-7a08c539d70a41d6bf0f14ce0971f0f3
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415483B2

Reaction notes

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