Triethylamine → HCID 19879242, compound

HRID 359716Notes

Reaction equation

HRID 359716 reaction equation
C(OCC1C=C(C2N=C3CCCN3C=2C2C=CN=CC=2)SC=1)(=O)C.[SH:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[N:33]=[C:34]3[CH2:45][CH2:44][CH2:43][N:35]3[C:36]=2[C:37]2[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=2)=[CH:28][CH:27]=1.C(N(CC)CC)C.[CH:53]1[CH:58]=[CH:57][C:56]([O:59][C:60](Cl)=[S:61])=[CH:55][CH:54]=1>COCCOCCOC>[O:59]([C:60]([S:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]2[N:33]=[C:34]3[CH2:45][CH2:44][CH2:43][N:35]3[C:36]=2[C:37]2[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=2)=[CH:30][CH:31]=1)=[S:61])[C:56]1[CH:57]=[CH:58][CH:53]=[CH:54][CH:55]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 70498Phenyl thioxochloroformateHCID 70072163HCID 70072163, compoundHCID 135962046(4-mercaptophenyl) 3 (4-pyridyl) 6,7dihydro[5H]-pyrrolo[1,2-a]imidazole

Product 1

HCID 19879242HCID 19879242, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

To an ice-bath cooled solution containing 1.0 q (3.4mmole) of 2 (4-mercaptophenyl) 3 (4-pyridyl) 6,7dihydro[5H]-pyrrolo[1,2-a]imidazole prepared as in Example 16 and 0.5 ml (3.6 mmole) of triethylamine in 10 ml of diglyme is added 0.48 ml (3.5mmole) of phenyl chlorothionoformate. The reaction is allowed to warm to room temperature and heated at 40° to 120° C. for several hours. Workup and chromatography in a manner analogous to that outlined in Example 18 affords the desired titled compound.

Workup

  1. temperatureTo an ice-bath cooled solution
  2. additioncontaining
  3. temperatureheated at 40° to 120° C. for several hours

Sources & evidence

ORD record
ord-c8959db043e745d4b960580110aca870
Source dataset
uspto-grants-1991_03
Patent number
US05002941

Reaction notes

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