Hydrogen Sulfide → ethyl N-[N-(4-thiocarbamoylbenzoyl)carbamoyl]piperidin-4-yloxyacetate

HRID 1900914Notes

Reaction equation

HRID 1900914 reaction equation
[C:1]([C:3]1[CH:26]=[CH:25][C:6]([C:7]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][CH:15]([O:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:14][CH2:13]2)=[O:11])=[O:8])=[CH:5][CH:4]=1)#[N:2].N1C=CC=CC=1.[SH2:33]>C(N(CC)CC)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]([N:12]2[CH2:13][CH2:14][CH:15]([O:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:16][CH2:17]2)=[O:11])=[O:8])=[CH:25][CH:26]=1)(=[S:33])[NH2:2]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 1049PyridineHCID 23369999ethyl N-[N-(4-cyanobenzoyl)carbamoyl]piperidin-4-yloxyacetate

Product 1

HCID 23370050ethyl N-[N-(4-thiocarbamoylbenzoyl)carbamoyl]piperidin-4-yloxyacetate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a similar manner to Example 1, starting material step (b), the product from step (c) (1.2 g), pyridine (84 ml), triethylamine (7 ml) and H2S gas were reacted to give ethyl N-[N-(4-thiocarbamoylbenzoyl)carbamoyl]piperidin-4-yloxyacetate (0.74 g) as a yellow gum: NMR Spectrum (DMSO-d6) 1.20 (3H, t), 1.50 (2H, m), 1.87 (2H, m), 3.20 (2H, m), 3.66 (3H, m), 4.12 (2H, q), 4.15 (2H, s), 7.90 (4H, m), 9.63 (1H, br s), 10.00 (1H, br s); Mass Spectrum m/Z 394 (M+H)+.

Sources & evidence

ORD record
ord-488c60ac063e41f28cb60013dc95e50a
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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