Methyl chloroformate → HCID 69801425, compound

HRID 1072528Notes

Reaction equation

HRID 1072528 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:15]=[C:16]([NH2:20])[CH:17]=[CH:18][CH:19]=1.[Ar].Cl[C:23]([O:25][CH3:26])=[O:24].C(OCl)=O>ClCCl>[ClH:1].[CH3:26][O:25][C:23](=[O:24])[NH:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([CH:5]2[C:4]3[C:9](=[C:10]([Cl:12])[CH:11]=[C:2]([Cl:1])[CH:3]=3)[CH2:8][N:7]([CH3:13])[CH2:6]2)[CH:15]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 22382373HCID 22382373, compoundHCID 88000611HCID 88000611, compound

Product 1

HCID 69801425HCID 69801425, compoundYield 230.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under stirring and argon 3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydro-isoquinolin-4-yl)-phenylamine (15 mg, example 35) was dissolved in dichloromethane (1.5 ml) and methyl chloroformate (4.6 mg) dissolved in dichloromethane (0.5 ml) was added. After stirring for 6 h and standing over night additional chloro formate (2.3 mg) was added. Stirring was continued for 5 h, then the solvent was removed and the residue was dissolved in water/2N hydrochloric acid and freeze dried to give 20 mg of the title compound.

Workup

  1. additionwas added
  2. stirringAfter stirring for 6 h
  3. waitstanding over night
  4. stirringStirring
  5. customthe solvent was removed
  6. dissolutionthe residue was dissolved in water/2N hydrochloric acid
  7. customfreeze dried

Sources & evidence

ORD record
ord-678b811799c2460ca50f3ac003a5b585
Source dataset
uspto-grants-2005_06
Patent number
US06911453B2

Reaction notes

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