Chlorosuccinimide → HCID 21255151, compound

HRID 636563Notes

Reaction equation

HRID 636563 reaction equation
[Cl:1]N1C(=O)CCC1=O.[S:9]1[C:13]([C:14]2[N:22]3[C:17]([CH2:18][CH2:19][CH2:20][CH2:21]3)=[C:16]([C:23]([NH2:25])=[O:24])[CH:15]=2)=[CH:12][N:11]=[CH:10]1>C(#N)C.C(OCC)C>[Cl:1][C:15]1[C:16]([C:23]([NH2:25])=[O:24])=[C:17]2[N:22]([C:14]=1[C:13]1[S:9][CH:10]=[N:11][CH:12]=1)[CH2:21][CH2:20][CH2:19][CH2:18]2

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 21255178HCID 21255178, compound

Product 1

HCID 21255151HCID 21255151, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

N-Chlorosuccinimide is added in 0.05 g portions to a solution of 0.1 g of 3-(5-thiazolyl)-5,6,7,8-tetrahydroindolizine-1-carboxamide in 10 cm3 of acetonitrile at 65° C. After 2 hours a precipitate is seen to form. The mixture is allowed to cool to approximately 20° C., the solid is filtered off and washed with two times 0.5 cm3 of acetonitrile. The operation was repeated another two times on 0.1 g of 3-(4-thiazolyl)-5,6,7,8-tetrahydroindolizine-1-carboxamide. The solids obtained in the three tests were combined and chromatographed on a column of 1.8 cm diameter containing 40 g of silica (0.063-0.220). Elution is carried out with a 95/5 mixture of dichloromethane and methanol, 2-cm3 fractions being collected. The homogeneous fractions are combined and concentrated at reduced pressure (2.7 kPa) at a temperature close to 40° C., to give a white solid which is taken up in ethyl ether and then filtered off and dried in air. 0.12 g of 2-chloro-3-(5-thiazolyl)-5,6,7,8-tetrahydroindolizine-1-carboxamide are thus obtained in the form of a white solid which melts at 227° C.

Workup

  1. customto form
  2. filtrationthe solid is filtered off
  3. washwashed with two times 0.5 cm3 of acetonitrile
  4. customThe solids obtained in the three tests
  5. customchromatographed on a column of 1.8 cm diameter
  6. additioncontaining 40 g of silica (0.063-0.220)
  7. washElution
  8. additionis carried out with a 95/5 mixture of dichloromethane and methanol, 2-cm3 fractions
  9. custombeing collected
  10. concentrationconcentrated at reduced pressure (2.7 kPa) at a temperature
  11. customclose to 40° C.
  12. customto give a white solid which
  13. filtrationfiltered off
  14. customdried in air

Sources & evidence

ORD record
ord-6043ae13fe1443fdb1df3a817d0929dc
Source dataset
uspto-grants-2001_02
Patent number
US06194426B1

Reaction notes

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