Phosgene → HCID 88014990, compound

HRID 370039Notes

Reaction equation

HRID 370039 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[N:5]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C@H:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[CH:14]=2)[NH:9][C@@H:8]([CH3:20])[CH2:7]1)[CH3:2].[C:29](Cl)([Cl:31])=[O:30]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:28])[N:5]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C@H:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[CH:14]=2)[N:9]([C:29]([Cl:31])=[O:30])[C@@H:8]([CH3:20])[CH2:7]1)[CH3:2]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 69832857HCID 69832857, compound

Product 1

HCID 88014990HCID 88014990, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of cis-benzyl-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl)-carbamic acid ethyl ester (Example 66) (103 mg, 0.268 mmol) in toluene (2.5 mL) was added phosgene (1.0 mL of a 1.93M solution in toluene) and the reaction mixure was heated at reflux for 2 h. The reaction mixture was then concentrated in vacuo to give the desired carbamoyl chloride (110 mg, 92%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-925b413a15fe4625a0422ad5ef55a901
Source dataset
uspto-grants-2000_10
Patent number
US06140342

Reaction notes

Loading…