1-Chloroethyl chloroformate → HCID 70170259, compound

HRID 2188210Notes

Reaction equation

HRID 2188210 reaction equation
[CH2:1]([N:8]([CH2:10][C@H:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)[CH:17]=2)[C@H:12]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)C)C1C=CC=CC=1.[Cl:32]C(OC(Cl)=O)C>ClCCl>[ClH:32].[CH3:1][NH:8][CH2:10][C@H:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)[CH:17]=2)[C@H:12]1[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 70168191HCID 70168191, compound

Product 1

HCID 70170259HCID 70170259, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of cis-2-(N-benzyl-N-methylamino)methyl-1-phenyl-1,2,3,4-tetrahydro-6-(2-thienyl)naphthalene (727 mg) in dichloromethane (75 cm3) which was being maintained at 0° C. under nitrogen was added 1-chloroethylchloroformate (0.208 cm3) dropwise. The mixture was then allowed to warm to room temperature, before being heated to reflux. After approximately 2 h analysis of the reaction mixture indicated complete consumption of the starting material. The dichloromethane was evaporated and the residue was then taken up into methyl alcohol and heated to reflux for 1 h. The solvent was evaporated to afford the title compound which was used in the next reaction without further purification; positive ion ESI (M+H)+ 334.2.

Workup

  1. temperaturebefore being heated to reflux
  2. customconsumption of the starting material
  3. customThe dichloromethane was evaporated
  4. temperatureheated
  5. temperatureto reflux for 1 h
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-5995eefad9b143aea1f94328428250c6
Source dataset
uspto-grants-2002_06
Patent number
US06410592B1

Reaction notes

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