Methylamine → HCID 18992010, compound

HRID 375749Notes

Reaction equation

[C:1]1([C:7]2([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:11][C:10]3[CH:12]=[CH:13][C:14]([C:16]([O-])=[O:17])=[CH:15][C:9]=3[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[N:26]1(OC(N(C)C)=[N+](C)C)[C:30]2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.CN>CN(C)C=O>[CH3:30][NH:26][C:16]([C:14]1[CH:13]=[CH:12][C:10]2[O:11][C:7]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[O:8][C:9]=2[CH:15]=1)=[O:17]

Participants

Conditions

Temperature: 20 °C

Procedure

To a suspension of 23.0 g of lithium 2,2-diphenyl-1,3-benzodioxole-5-carboxylate in 200 ml of dimethylformamide were added 27.0 g of O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium-hexafluorophosphate. The mixture was stirred at 20° C. for 2 hours, then 25 ml of methylamine were added, and stirring was continued for another 2 hours. The mixture was partitioned between ethyl acetate and water, the organic layer was washed successively with 2N potassium hydrogensulfate solution, saturated sodium carbonate solution and brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the solid residue was crystallized from ethanol to give 15.6 g of N-methyl-2,2-diphenyl-1,3-benzodioxole-5-carboxamide, m.p. 144°-145° C.

Workup

stirringstirring
waitwas continued for another 2 hours
customThe mixture was partitioned between ethyl acetate and water
washthe organic layer was washed successively with 2N potassium hydrogensulfate solution, saturated sodium carbonate solution and brine
dry with materialdried over magnesium sulfate
customThe solvent was evaporated in vacuo
customthe solid residue was crystallized from ethanol

Sources & evidence

ORD record: ord-45576da300174e1d8c6253121208e101
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05486466

Reaction notes

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