1-Chloroethyl chloroformate → HCID 86603628, compound

HRID 2376005Notes

Reaction equation

HRID 2376005 reaction equation
[Cl:1]C(OC(Cl)C)=O.C([N:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22]2[S:23][CH:24]=[C:25](/[CH:27]=[CH:28]/[C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:26]=2)[CH2:17][CH2:16]1)C1C=CC=CC=1>ClCCl>[ClH:1].[ClH:1].[NH:15]1[CH2:16][CH2:17][CH:18]([NH:21][C:22]2[S:23][CH:24]=[C:25](/[CH:27]=[CH:28]/[C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:26]=2)[CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 86603630HCID 86603630, compound

Product 1

HCID 86603628HCID 86603628, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Chloroethyl chloroformate (1.88 mL) was added a mixture of ethyl (2E)-3-(2-[(1-benzyl-4-piperidyl)amino]-1,3-thiazol-4-yl)acrylate (2.7 g) in dichloromethane (40 mL) at ambient temperature and the mixture was stirred at same temperature for 1.5 hour. The solvent was removed by concentration. To the residue was added an EtOH (42.7 mL) and the mixture was stirred at 70° C. for 2 hours. The reaction mixture was added 2N-ethanolic hydrogen chloride (7.3 mL) at ambient temperature and the mixture was stirred at same temperature for 20 hours. The isolated precipitate was collected by filtration to give ethyl (2E)-3-[2-(4-piperidylamino)-1,3-thiazol-4-yl]acrylate dihydrochloride (1.44 g).

Workup

  1. customThe solvent was removed by concentration
  2. additionTo the residue was added an EtOH (42.7 mL)
  3. stirringthe mixture was stirred at 70° C. for 2 hours
  4. additionThe reaction mixture was added 2N-ethanolic hydrogen chloride (7.3 mL) at ambient temperature
  5. stirringthe mixture was stirred at same temperature for 20 hours
  6. filtrationThe isolated precipitate was collected by filtration

Sources & evidence

ORD record
ord-654b0f3d98254332aeaecb1cf08d99a7
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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