Dimethylformamide → HCID 17995130, compound

HRID 1638549Notes

Reaction equation

O=[C:2]1[CH2:8][CH2:7][CH2:6][C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[NH:3]1.[H-].[Na+].CCOP(Cl)(OCC)=O.[CH2:24]([C:26]1[O:30][N:29](C)[CH:28]([N+]#[C-])[N:27]=1)[CH3:25].[CH3:34][N:35](C=O)[CH3:36]>C(O)(=O)C>[CH2:24]([C:26]1[O:30][N:29]=[C:28]([C:34]2[N:35]=[CH:36][N:3]3[C:4]4[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=4[CH2:6][CH2:7][CH2:8][C:2]=23)[N:27]=1)[CH3:25]

Participants

Conditions

Temperature: -20 °C

Procedure

2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine (10 mmol) was dissolved in dry DMF (15 ml) and charged with sodium hydride (13 mmol. The resulting solution was cooled under N2 to -20° C., whereafter chlordiethylphosphate (13 mmol) was added. The reaction mixture was kept under N2 with stirring at -20° C. and was charged with a -30° C. cold solution of 5-ethyl-3-isocyano-methyl-1,2,4-oxadiazol (13 mmol) and K-t-butylate (13 mmol) in dry DMF (10 ml). The resulting reaction mixture was allowed to heat to room temperature, whereafter 5 ml of glacial acetic acid was added. The resulting mixture was filtered which gave 0.36 g of the title compound. M.p. 150.7°-150.8° C.

Workup

additionwas added
customThe resulting reaction mixture
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filtrationThe resulting mixture was filtered which

Sources & evidence

ORD record: ord-e8c1bba690034acaa0b3353d5ed331af
Source dataset: uspto-grants-1989_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04880799

Reaction notes

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