Potassium Carbonate → HCID 22592088, compound

HRID 746634Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:12][C:13]1[C:14]([S:19][CH3:20])=[N:15][CH:16]=[CH:17][CH:18]=1)=[O:11].[SH:21][C:22]1[O:23][C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C=O)C>[O:23]1[C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=[C:22]1[S:21][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:12][C:13]1[C:14]([S:19][CH3:20])=[N:15][CH:16]=[CH:17][CH:18]=1)=[O:11]

Participants

Conditions

Temperature: 80 °C

Procedure

To a DMF (5 ml) solution of this amide (90 mg, 0.25 mmol) and 2-mercaptobenzoxazole (38 mg, 0.25 mmol) were added potassium carbonate (42 mg, 0.30 mmol) and 18-crown-6 (7 mg, 0.03 mmol), and the mixture was stirred at 80° C. for 3 hours. The reaction mixture was allowed to cool, and then extracted with ethyl acetate. The organic layer was washed with water and then with a saturated aqueous solution of sodium chloride, and dried over sodium sulfate. Subsequently, the solvent was distilled off, and the resulting residue was recrystallized from a mixture of ethyl acetate-hexane to obtain 83 mg (yield 77%) of the desired compound as a colorless powdery crystal.

Workup

temperatureto cool
extractionextracted with ethyl acetate
washThe organic layer was washed with water
dry with materialwith a saturated aqueous solution of sodium chloride, and dried over sodium sulfate
distillationSubsequently, the solvent was distilled off
customthe resulting residue was recrystallized from a mixture of ethyl acetate-hexane

Sources & evidence

ORD record: ord-934b2d2711534007be8abdf1dc8261ac
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07393866B2

Reaction notes

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