2-Methyl-2-thiopseudourea → HCID 74021304, compound

HRID 1867250Notes

Reaction equation

[CH3:1][S:2][C:3](=[NH:5])[NH2:4].[OH-:6].[Na+].Cl[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=[O:10]>C(Cl)Cl>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([CH2:12][O:11][C:9]([NH:5][C:3](=[N:4][C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=2)=[O:6])[S:2][CH3:1])=[O:10])=[CH:14][CH:15]=1)([O-:21])=[O:20]

Participants

Conditions

Temperature: 0 °C

Procedure

To a clean 3-necked round bottom flask equipped with two addition funnels were added DCM (60 mL), S-methylisothiourea (1 g, 7.18 mmol), and 6.25N NaOH solution (aq, 570 uL). After cooling the resulting mixture to 0° C., a solution of 4-nitrobenzyl chloroformate (3.17 g, 14.73 mmol) in DCM (20 mL) and a solution of sodium hydroxide (aq, 1N, 15 mL) were simultaneously added dropwise using the two addition funnels while maintaining pH 11. The mixture was aged for 16 h with gradual warming to rt. The layers were separated and the organic phase was washed with brine (20 mL) and dried over sodium sulfate. Solvent was removed under vacuum and the resulting white solid recrystallized from ethyl acetate and hexanes to give 132 (2.7 g, 84%) as a white powder.

Workup

customTo a clean 3-necked round bottom flask equipped with two addition funnels
additionthe two addition funnels
temperaturewhile maintaining pH 11
temperaturewith gradual warming to rt
customThe layers were separated
washthe organic phase was washed with brine (20 mL)
dry with materialdried over sodium sulfate
customSolvent was removed under vacuum
customthe resulting white solid recrystallized from ethyl acetate and hexanes

Sources & evidence

ORD record: ord-8ee0a42a54a44916be49c60d0f0b57b2
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07632828B2

Reaction notes

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