1-Chloroethyl chloroformate → HCID 86603628, compound

HRID 226320Notes

Reaction equation

HRID 226320 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-155b84b7e94f40b1aa320dc59f620f10
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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