Potassium Carbonate → HCID 68278111, compound

HRID 1526900Notes

Reaction equation

Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8].[O:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([S:34]([O-:36])=[O:35])=[CH:30][CH:29]=2)[CH2:21][CH2:20]1.[Li+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:8][C:7]1[O:6][C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)=[N:4][C:3]=1[CH2:2][S:34]([C:31]1[CH:32]=[CH:33][C:28]([CH2:27][CH2:26][CH2:25][N:22]2[CH2:23][CH2:24][O:19][CH2:20][CH2:21]2)=[CH:29][CH:30]=1)(=[O:35])=[O:36]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of methyl 4-(4-(chloromethyl)-5-methyloxazol-2-yl)benzoate (2.0 g, 7.55 mmol, 1.00 equiv), lithium 4-(3-morpholinopropyl)benzenesulfinate (4.0 g, 14.55 mmol, 1.93 equiv) and potassium carbonate (1.35 g, 9.78 mmol, 1.30 equiv) in N,N-dimethylformamide (50 mL) was stirred overnight at 70° C. The product was precipitated by the addition of 150 mL ice and water after the reaction was cooled to room temperature. The solid was collected by filtration, washed with 2×15 mL of water and dried in a vacuum oven to give 2.8 g (74%) of methyl 4-(5-methyl-4-((4-(3-morpholinopropyl)phenylsulfonyl)methyl)oxazol-2-yl)benzoate as a white solid. LC-MS: (ES, m/z): 499 [M+H]+, 115.

Workup

customThe product was precipitated by the addition of 150 mL ice and water after the reaction
temperaturewas cooled to room temperature
filtrationThe solid was collected by filtration
washwashed with 2×15 mL of water
customdried in a vacuum oven

Sources & evidence

ORD record: ord-1b69ea8ee810449e87f901fd34fd081c
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085570B2

Reaction notes

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