Lawesson's reagent → HCID 50992124, compound

HRID 1929508Notes

Reaction equation

[NH2:1][C:2]1[CH2:7][O:6][CH2:5][C:4]([C:9]2[CH:10]=[C:11]([NH:16][C:17](=O)[C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[CH:12]=[CH:13][C:14]=2[F:15])([CH3:8])[N:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:35])=CC=1>COCCOC>[NH2:1][C:2]1[CH2:7][O:6][CH2:5][C:4]([C:9]2[CH:10]=[C:11]([NH:16][C:17](=[S:35])[C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[CH:12]=[CH:13][C:14]=2[F:15])([CH3:8])[N:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of (RS)-N-[3-(5-amino-3-methyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-4-chloro-benzamide (0.056 g, 0.2 mmol) in 1,2-dimethoxyethane (2 ml) was treated with Lawesson's reagent (0.083 g, 0.2 mmol). After heating to 70° C. the dispersion turned into solution; the temperature was kept during 16 hours. Another 0.5 eq of Lawesson's reagent were added to complete the reaction and heating was continued at 80° C. After 2 days the reaction was still incomplete. For the workup, the reaction mixture was evaporated to dryness and the residue directly purified by chromatography on an Isolute flash NH2 column using a gradient of dichloromethane/methanol=100/0 to 90/10 as the eluent. There were obtained 0.006 g (10% of theory) of (RS)-N-[3-(5-amino-3-methyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-4-chloro-thiobenzamide (27) as a yellow solid. Mass (calculated) C18H17ClFN3OS [377.87]; (found) [M+H]+=378.

Workup

customthe reaction
temperatureheating
customwas continued at 80° C
waitAfter 2 days the reaction was still incomplete
customFor the workup, the reaction mixture was evaporated to dryness
customthe residue directly purified by chromatography on an Isolute flash NH2 column

Sources & evidence

ORD record: ord-f11093776c3440b89484c290eb1426e7
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188079B2

Reaction notes

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