HCID 21712663, compound → HCID 15501266, compound

HRID 650607Notes

Reaction equation

HRID 650607 reaction equation
C[O:2][C:3]([CH2:5][S:6][C:7]1[S:8][C:9]([C:15]([O:17][CH3:18])=[O:16])=[CH:10][C:11]=1[N+:12]([O-])=O)=O>C(O)(=O)C.O.[Fe]>[CH3:18][O:17][C:15]([C:9]1[S:8][C:7]2[S:6][CH2:5][C:3](=[O:2])[NH:12][C:11]=2[CH:10]=1)=[O:16]

Participants

5

Reactant 1

HCID 21712663HCID 21712663, compound

Product 1

HCID 15501266HCID 15501266, compoundYield 54.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-methoxycarbonylmethylthio-5-methoxycarbonyl-3-nitrothiophene (26.1 g) in acetic acid (360 ml) and water (36 ml) was added portionwise iron (36.5 g) at 80° C. After stirring for 3 hours at 80° C., the hot reaction mixture was filtered and the filtrate was poured into ice-water. The resulting precipitate was collected by filtration and washed with water to give 2,3-dihydro-6-methoxycarbonyl-2-oxothieno[2,3-b][1,4] thiazine (11.12 g).

Workup

  1. filtrationthe hot reaction mixture was filtered
  2. additionthe filtrate was poured into ice-water
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-d710ddbd93ad41cca5ebf52ecf992546
Source dataset
uspto-grants-2001_08
Patent number
US06274619B1

Reaction notes

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