Phosgene → HCID 59334899, compound

HRID 1517935Notes

Reaction equation

HRID 1517935 reaction equation
[C:1](Cl)(Cl)=[O:2].C(N(C(C)C)CC)(C)C.[Cl:14][C:15]1[CH:16]=[C:17]([S:22]([N:25]([CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:26]2[CH:27]=[C:28]3[C:32](=[CH:33][CH:34]=2)[NH:31][CH2:30][CH2:29]3)(=[O:24])=[O:23])[CH:18]=[C:19]([Cl:21])[CH:20]=1.[CH3:43][N:44]([CH3:48])[CH2:45][CH2:46][NH2:47]>C1(C)C=CC=CC=1.ClCCl.O1CCCC1.C(OCC)(=O)C>[Cl:14][C:15]1[CH:16]=[C:17]([S:22]([N:25]([CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:26]2[CH:27]=[C:28]3[C:32](=[CH:33][CH:34]=2)[N:31]([C:1](=[O:2])[NH:47][CH2:46][CH2:45][N:44]([CH3:48])[CH3:43])[CH2:30][CH2:29]3)(=[O:24])=[O:23])[CH:18]=[C:19]([Cl:21])[CH:20]=1

Participants

9

Reactant 4

HCID 6371PhosgeneHCID 66053N,N-DimethylethylenediamineHCID 81531DiisopropylethylamineHCID 59334895HCID 59334895, compound

Product 1

HCID 59334899HCID 59334899, compound

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

800 μl of a 20% solution of phosgene in toluene are dissolved in 10 ml dichloromethane and cooled to 0° C. To this are added 35 μl diisopropylethylamine and 100 mg tert.butyl [(3,5-dichloro-phenylsulphonyl)-(2,3-dihydro-1H-indol-5-yl)-amino]-acetate. The mixture is stirred for a further 1 hour and then the solvents are eliminated in a nitrogen current. The residue is taken up in 10 ml of tetrahydrofuran, 200 μl N,N-dimethylethylenediamine are added and the mixture is stirred for 3 hours at ambient temperature. Then it is diluted with ethyl acetate and washed with semi-saturated sodium chloride solution. The organic phase is dried on magnesium sulphate, the solvents are eliminated in vacuo and the residue is purified by chromatography on aluminum oxide (cyclohexane/ethyl acetate 3:7 to ethyl acetate).

Workup

  1. stirringthe mixture is stirred for 3 hours at ambient temperature
  2. washwashed with semi-saturated sodium chloride solution
  3. customThe organic phase is dried on magnesium sulphate
  4. customthe residue is purified by chromatography on aluminum oxide (cyclohexane/ethyl acetate 3:7 to ethyl acetate)

Sources & evidence

ORD record
ord-89cf7122f30b4fb49732cf8728c12f8f
Source dataset
uspto-grants-2012_07
Patent number
US08232312B2

Reaction notes

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