Methoxymethyl isocyanate → HCID 49868655, compound

HRID 570969Notes

Reaction equation

N([O-])=O.[Na+].S1C=CC=C1/C=C/C1N=CNC=1N.[CH3:18][O:19][CH2:20][N:21]=[C:22]=[O:23].[N+:24](=[C:26]1[C:30](/[CH:31]=[CH:32]/[C:33]2[S:34][CH:35]=[CH:36][CH:37]=2)=[N:29][CH:28]=[N:27]1)=[N-:25]>O.[H+].[B-](F)(F)(F)F.CS(C)=O>[CH3:18][O:19][CH2:20][N:21]1[C:22](=[O:23])[N:27]2[CH:28]=[N:29][C:30](/[CH:31]=[CH:32]/[C:33]3[S:34][CH:35]=[CH:36][CH:37]=3)=[C:26]2[N:24]=[N:25]1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium nitrite (150 mg, 2.1 mmol) in water (1 mL) was added to a suspension of (E)-4-(2-(thiophen-2-yl)vinyl)-1H-imidazol-5-amine (0.35 g, 1.8 mmol) in 10% HBF4 (4 mL) at 0° C. After stirring at 0° C. for 60 minutes, the precipitate was filtered from solution and dried over P2O5. This diazo compound (IR stretch 2193 cm−1) was used without further purification. Methoxymethyl isocyanate (0.43 g, 4.9 mmol) was added to a solution of (E)-4-diazo-5-(2-(thiophen-2-yl)vinyl)-4H-imidazole (0.3 g, 1.47 mmol) in dry DMSO (2 mL) under nitrogen. The resulting solution was stirred at room temperature for 48 hours, then purified by column chromatography (DCM) to give the title compound as a yellow solid (50 mg, 12%). δH (CDCl3) 8.44 (1H, s), 7.95 (1H, d, J=15.6), 7.34 (1H, d, J=5.1), 7.31 (1H, d, J=15.6), 7.26 (1H, d, J=3.6), 7.08 (1H, dd, J=5.1, 3.6), 5.69 (2H, s), 3.57 (3H, s).

Workup

filtrationthe precipitate was filtered from solution
dry with materialdried over P2O5
customThis diazo compound (IR stretch 2193 cm−1) was used without further purification
stirringThe resulting solution was stirred at room temperature for 48 hours
custompurified by column chromatography (DCM)

Sources & evidence

ORD record: ord-6ebd8a9a70cd488e81256b74502250da
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024018B2

Reaction notes

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