1-Chloroethyl chloroformate → HCID 19075290, compound

HRID 865140Notes

Reaction equation

HRID 865140 reaction equation
[Cl:1][C:2]1[C:6]([C:7]2[CH2:8][N:9](C)[CH2:10][CH2:11][CH:12]=2)=[N:5][S:4][N:3]=1.ClC(OC(Cl)=O)C>ClCCCl>[ClH:1].[Cl:1][C:2]1[C:6]([C:7]2[CH2:8][NH:9][CH2:10][CH2:11][CH:12]=2)=[N:5][S:4][N:3]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 14936861HCID 14936861, compound

Product 1

HCID 19075290HCID 19075290, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of 3-(3-chloro-1,2,5-thiadiazol-4-yl)-1,2,5,6-tetrahydro-1-methylpyridine (670 mg, 3.1 mmol) in 1,2-dichloroethane (20 ml) was added a solution of 1-chloroethyl-chloroformate (440 mg, 3.1 mmol) in 1,2-dichloroethane at 0° C. The reaction mixture was heated to 40° C. for 2 h and evaporated. The residue was dissolved in methanol and heated to reflux for 1 h. After cooling to room temperature the precipitate was collected by filtration to yield 320 mg (41%). (M.p. 224° C.; M+ : 201 and 203; Compound 17).

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in methanol
  3. temperatureheated
  4. temperatureto reflux for 1 h
  5. temperatureAfter cooling to room temperature the precipitate
  6. filtrationwas collected by filtration
  7. customto yield 320 mg (41%)

Sources & evidence

ORD record
ord-d1fe37f1414040c196b3bb01c26f056c
Source dataset
uspto-grants-1996_10
Patent number
US05565475

Reaction notes

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