Hydrochloric Acid → N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-formylbenzenesulfonamide

HRID 1164174Notes

Reaction equation

[H-].COCCO[Al+]OCCOC.[Na+].[H-].N1CCOCC1.[CH3:21][O:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[N:26]=[C:25]([NH:31][C:32]([NH:34][S:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[C:44](OC)=[O:45])(=[O:37])=[O:36])=[O:33])[N:24]=1.Cl>O1CCCC1>[CH3:21][O:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[N:26]=[C:25]([NH:31][C:32]([NH:34][S:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[CH:44]=[O:45])(=[O:37])=[O:36])=[O:33])[N:24]=1

Participants

Conditions

Temperature: -40 °C

Procedure

A mixture of 3.0 g of sodium bis(2-methoxyethoxy)aluminum hydride and 0.9 g of morpholine in 25 ml of dry tetrahydrofuran was cooled to -40° C. and 1.0 g of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide was added. The resulting clear homogeneous solution was allowed to warm to room temperature over a period of 2 hours. Dilute hydrochloric acid was added and the mixture was extracted with methylene chloride. The organic extracts were washed, dried and evaporated. The crude product, which contained the desired aldehyde, the unreacted ester and the over-reduced alcohol, was purified by means of dry column chromatography. The purified product had a m.p. of 180° C.

Workup

temperatureto warm to room temperature over a period of 2 hours
extractionthe mixture was extracted with methylene chloride
washThe organic extracts were washed
customdried
customevaporated
customthe unreacted ester and the over-reduced alcohol, was purified by means of dry column chromatography

Sources & evidence

ORD record: ord-2f724c0b47d04a6faf313899d03787b4
Source dataset: uspto-grants-1983_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04368069

Reaction notes

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