Phosphorus sulfide (P2S5) → HCID 178463820, compound

HRID 1090248Notes

Reaction equation

HRID 1090248 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=S.[CH2:15]([N:17]([CH2:41][CH3:42])[CH:18]1[CH:23]([CH3:24])[CH2:22][CH:21]([C:25]2[C:30]3[C:31](S)=[N:32][C:33]4=[CH:34][CH:35]=[CH:36][C:28]([C:29]=34)=[CH:27][CH:26]=2)[CH:20]([CH:38]([CH3:40])[CH3:39])[CH2:19]1)[CH3:16].[N:43]1([CH2:48][CH2:49][CH2:50][NH2:51])[CH:47]=[CH:46][N:45]=[CH:44]1>C(O)C>[CH2:15]([N:17]([CH2:41][CH3:42])[CH:18]1[CH:23]([CH3:24])[CH2:22][CH:21]([C:25]2[C:30]3[C:31]([NH:51][CH2:50][CH2:49][CH2:48][N:43]4[CH:47]=[CH:46][N:45]=[CH:44]4)=[N:32][C:33]4=[CH:34][CH:35]=[CH:36][C:28]([C:29]=34)=[CH:27][CH:26]=2)[CH:20]([CH:38]([CH3:40])[CH3:39])[CH2:19]1)[CH3:16]

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 787361H-Imidazole-1-propanamineHCID 178463821HCID 178463821, compound

Product 1

HCID 178463820HCID 178463820, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Bromobenz(cd)indol-2-(1H)-one is treated with ethyl chloroformate in alkaline solution to yield the N-carbethoxy derivative. Successive reactions with magnesium, formaldehyde, and 48% hydrobromic acid leads to 6-bromomethylbenz(cd)indol-2(1H)-one, which on treatment with diethylamine yields the 6-diethylaminomethyl derivative. Treatment with P2S5 in refluxing pyridine leads to 6-diethylaminomenthylbenz(cd)indol-2-thiol, which on reaction with molar equivalents of 3-(1H-imidazol-1yl)propanamine and mercuric acetate in refluxing ethanol, under the conditions of Example 55, leads to the preparation of the title compound.

Sources & evidence

ORD record
ord-49b636978259404da3257088e807eea8
Source dataset
uspto-grants-1992_01
Patent number
US05081131

Reaction notes

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