2-Methyltetrahydrofuran → HCID 178465554, compound

HRID 2054380Notes

Reaction equation

[OH-].[Na+].CC1CCCO1.C(O)(=O)C.[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:21]=[C:22]([NH:25][C:26](=[NH:28])[CH3:27])[NH:23][N:24]=1>CC(OC)(C)C>[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:21]=[C:22]([NH:25][C:26](=[NH:28])[CH3:27])[NH:23][N:24]=1

Participants

Conditions

Temperature: -5 °C

Procedure

To a stirred mixture of 2 M aqueous NaOH (75 mL, 152 mol) and 2-methyltetrahydrofuran (155 ml) was added N-[5-(2-chlorophenyl)-2H-pyrazol-3-yl]-acetamidine, acetate salt (I-1A-1a; 11.5 g, 39.0 mmol), portionwise, over 15 minutes at room temperature. The organic layer was separated, washed with brine (75 ml), and then concentrated to one half volume, at which time a precipitate begins to form. The stirred mixture was diluted with MTBE (70 mL), cooled to −5° C. in an ice/brine bath for 1 hour, and the resulting precipitate collected on a course sintered glass funnel. The solid was washed with ice cold MTBE (50 mL) and then dried, in vacuo, to afford intermediate I-1A-1b as a solid (5.74 g, 63%): +ESI MS (M+1) 235.3; 1H NMR (400 MHz, CD3OD) δ 7.56-7.53 (m, 1H), 7.48-7.44 (m, 1H), 7.36-7.28 (m, 2H), 6.27 (s, 1H), 2.04 (s, 3H).

Workup

customThe organic layer was separated
washwashed with brine (75 ml)
concentrationconcentrated to one half volume, at which time a precipitate
customto form
customthe resulting precipitate collected on a course sintered glass funnel
washThe solid was washed with ice cold MTBE (50 mL)
customdried, in vacuo

Sources & evidence

ORD record: ord-59479d8855224ff4b809fb7ae91e085e
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07329658B2

Reaction notes

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