Acetic Acid → HCID 54221264, compound

HRID 635851Notes

Reaction equation

HRID 635851 reaction equation
[Br-].CN([CH:5]=[N:6][C:7]1[S:8][C:9]2[CH2:20][CH2:19][CH2:18][C:10]=2[N+:11]=1[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])C.C1CCN2C(=NCCC2)CC1.C(O)(=O)C>CN(C=O)C>[CH2:16]([O:15][C:13]([C:12]1[N:11]2[C:7]([S:8][C:9]3[CH2:20][CH2:19][CH2:18][C:10]=32)=[N:6][CH:5]=1)=[O:14])[CH3:17]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86756426HCID 86756426, compound

Product 1

HCID 54221264HCID 54221264, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-[[(Dimethylamino)methylene]amino]-3-(2-ethoxy-2-oxoethyl)-5,6-dihydro-4H-cyclopentathiazolium bromide (Formula E-3) (4.0 g) in DMF (20 mL) dissolved on addition of DBU (2.48 mL). The solution was reacted at 25° for 18 hours, poured into cold 10% acetic acid solution, and precipitated 6,7-Dihydro-5H-cyclopent[d]imidazo[2,1-b]thiazole-3-carboxylic acid ethyl ester (Formula E-4) (1.95 g) was filtered. Crystallization of an aliquot from isopropanol gave pure 6,7-Dihydro-5H-cyclopent[d]imidazo[2,1-b]thiazole-3-carboxylic acid ethyl ester (Formula E-4), m.p. 101-102°.

Workup

  1. customThe solution was reacted at 25° for 18 hours
  2. customprecipitated 6,7-Dihydro-5H-cyclopent[d]imidazo[2,1-b]thiazole-3-carboxylic acid ethyl ester (Formula E-4) (1.95 g)
  3. filtrationwas filtered
  4. customCrystallization of an aliquot from isopropanol

Sources & evidence

ORD record
ord-66a5b476126b41148b7dd0635c965c50
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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