Methanol → HCID 21422780, compound

HRID 259061Notes

Reaction equation

[CH3:1][N:2]([O:19][CH3:20])[C:3]([O:5][C:6]1[CH:7]=[C:8]([CH:16]=[CH:17][CH:18]=1)[NH:9][C:10](=[O:15])[CH2:11][C:12](=[O:14])[CH3:13])=[O:4].[CH:21]([O-])([O-])[O:22]C.[CH3:26]O>C1(C)C=CC(S(O)(=O)=O)=CC=1.N1C2C(=CC=CC=2)C=CC=1>[CH3:1][N:2]([O:19][CH3:20])[C:3]([O:5][C:6]1[CH:7]=[C:8]([CH:16]=[CH:17][CH:18]=1)[NH:9][C:10](=[O:15])[CH2:11][C:12]([O:22][CH3:21])([O:14][CH3:26])[CH3:13])=[O:4]

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 32.5 g of m-(N-methyl-N-methoxy-carbamoyloxy)-acetylacetanilide, 0.4 g of p-toluene sulfonic acid, 32.5 g of methyl orthoformate and 60 ml of methanol was stirred for 24 hours at 20°C and after the addition of 0.4 g of quinoline, the mixture was evaporated to dryness to obtain 40 g of m-(N-methyl-N-methoxy-carbamoyloxy)-3,3-dimethoxy-butyranilide. The product was dissolved in 175 ml of toluene and the solution was heated at 140°C. for 5 hours while distilling off a toluene-methanol azeotrope. The mixture was then evaporated to dryness and the residue was chromatographed over silica gel. Elution with a 9-1 methylene chloride-acetone mixture yielded 11.5 g of m-(N-methoxy-carbamoyloxy)-3-methoxy-crotonanilide with a refractive index nD20 = 1.544.

Workup

customthe mixture was evaporated to dryness

Sources & evidence

ORD record: ord-d79ee03595a14b26985eacbef19d9794
Source dataset: uspto-grants-1977_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04036633

Reaction notes

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