HCID 21256459, compound → HCID 21256498, compound

HRID 635856Notes

Reaction equation

HRID 635856 reaction equation
[N:1]1[CH:2]=[C:3]([CH2:15][OH:16])[N:4]2[C:8]3[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:7]=3[S:6][C:5]=12>C1(C)C=CC=CC=1.O=[Mn]=O>[N:1]1[CH:2]=[C:3]([CH:15]=[O:16])[N:4]2[C:8]3[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:7]=3[S:6][C:5]=12

Participants

4

Reactant 1

HCID 21256459HCID 21256459, compound

Product 1

HCID 21256498HCID 21256498, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Procedure

A solution of 5,6,7,8,9,10-Hexahydrocyclooct[d]imidazo[2,1-b]thiazole-3-methanol (Formula H-5) (1.6 g) in hot toluene (250 mL) was treated with MnO2 (3.8 g) and azeotropically distilled for 1 hour. The cooled mixture was filtered and the combined filtrate and ethyl acetate washes were evaporated to yield pure 5,6,7,8,9,10-Hexahydro-cyclooct[d]imidazo[2,1-b]thiazole-3-carboxaldehyde (Formula H-6) (1.41 g), m.p. 106-107°, after crystallization from hexane.

Workup

  1. distillationazeotropically distilled for 1 hour
  2. filtrationThe cooled mixture was filtered
  3. customthe combined filtrate and ethyl acetate washes were evaporated

Sources & evidence

ORD record
ord-4be857b3f3d34ad989d862da983cfcef
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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