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

HRID 235563
Notes
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Reaction equation

HRID 235563 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 10810737N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamideHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 13097377N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-formylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

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

Sources & evidence

ORD record
ord-ae28bbe99f4648c1a2cede1f0bf812e3
Source dataset
uspto-grants-1987_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04640704

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes