Propionic Acid → HCID 15035101, compound

HRID 1090249Notes

Reaction equation

HRID 1090249 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.C(O)(=O)CC.[C:18]1([NH:24][C:25](=O)[CH2:26][CH2:27][N:28]2[CH:32]=[CH:31][N:30]=[CH:29]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.B.[N:35]1[C:43]2[C:38]3[C:39](=[CH:44][CH:45]=[CH:46][C:37]=3[C:36]=1S)[CH:40]=[CH:41][CH:42]=2>O1CCCC1>[N:28]1([CH2:27][CH2:26][CH2:25][N:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:36]2[C:37]3[CH:46]=[CH:45][CH:44]=[C:39]4[C:38]=3[C:43](=[CH:42][CH:41]=[CH:40]4)[N:35]=2)[CH:32]=[CH:31][N:30]=[CH:29]1

Participants

7

Reactant 5

HCID 1032Propionic AcidHCID 6331Borane2×HCID 682631,1'-CarbonyldiimidazoleHCID 19914575HCID 19914575, compound3×HCID 178527764HCID 178527764, compound

Product 1

HCID 15035101HCID 15035101, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

The reaction of 1,1'-carbonyldiimidazole and 3-(1e,uns/H/ -imidazol-1yl)propanoic acid in tetrahydrofuran solution, followed by treatment with aniline leads to the formation of N-phenyl-3-(1H-imidazol-1-yl)propanamide. Reduction with borane in tetrahydrofuran solution then gives N-phenyl-3-(1H-imidazol-1-yl)propanamide. Reduction with borane in tetrahydrofuran solution then gives N-phenyl-3-(1H-imidazol-1-yl)propanamide. The latter compound with molar equivalents of benz(cd)indol-2-thiol and mercuric acetate in refluxing ethanol leads tot eh formation of the title compound, under the conditions of Example 55.

Sources & evidence

ORD record
ord-e6b09787bb1f40bc84579938d0a86ea9
Source dataset
uspto-grants-1992_01
Patent number
US05081131

Reaction notes

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