Water → HCID 13186359, compound

HRID 1388304Notes

Reaction equation

HRID 1388304 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[S:10][CH:11]=[C:12]([CH2:14][S:15]([NH:18][C:19](=[O:23])[C:20]([O-])=[O:21])(=[O:17])=[O:16])[N:13]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].CC(C)([O-])C.[K+].O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[S:10][CH:11]=[C:12]([C:14]3[S:15](=[O:17])(=[O:16])[NH:18][C:19](=[O:23])[C:20]=3[OH:21])[N:13]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 962WaterHCID 20470852HCID 20470852, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 13186359HCID 13186359, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the ethyl oxamate intermediate prepared in Step E above (4.4 g., 0.010 mol) in dimethylformamide (26 ml) was added potassium tert-butoxide (3.5 g., 0.032 mol) in portions over 15 minutes. After stirring overnight, the reaction mixture was poured into water (250 ml). Acidification with 6 N hydrochloric acid, followed by filtration, yielded 3.5 g. of crude product. Recrystallization from tetrahydrofuran-ether-petroleum ether gave 1.74 g. of the title compound, m.p. 301° C. (dec.).

Workup

  1. filtrationAcidification with 6 N hydrochloric acid, followed by filtration
  2. customyielded 3.5 g
  3. customRecrystallization from tetrahydrofuran-ether-petroleum ether
  4. customgave 1.74 g

Sources & evidence

ORD record
ord-16e188cec2714c80b6cb28c007eb8d46
Source dataset
uspto-grants-1984_02
Patent number
US04431652

Reaction notes

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