Morpholine → HCID 68629109, compound

HRID 572624Notes

Reaction equation

HRID 572624 reaction equation
[C:1]([C:3]1[C:4]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)=[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[S:6][C:7]=1S(C)(=O)=O)#[N:2].[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>C1COCC1>[C:1]([C:3]1[C:4]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)=[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[S:6][C:7]=1[N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)#[N:2]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 68628578Ethyl 4-cyano-3-(3,4-dichlorophenyl)-5-(methylsulfonyl)thiophene-2-carboxylate

Product 1

HCID 68629109HCID 68629109, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 4-cyano-3-(3,4-dichlorophenyl)-5-(methylsulfonyl)thiophene-2-carboxylate (1.77 g, 4.38 mmol) and morpholine (1.91 mL, 21.9 mmol) in THF (40 mL) was stirred at rt under an atmosphere of argon for 3 days. A precipitate had formed and was filtered to give ethyl 4-cyano-3-(3,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylate (1.14 g, 63%). 1H NMR (400 MHz, d6-DMSO) δ: 7.67-7.74 (m, 2H), 7.37 (dd, 1H), 4.06 (q, 2H), 3.74-3.78 (m, 4H), 3.59-3.63 (m, 4H) and 1.06 (t, 3H).

Workup

  1. customA precipitate had formed
  2. filtrationwas filtered

Sources & evidence

ORD record
ord-a933bbc142874e42b69ac07aaafea2b0
Source dataset
uspto-grants-2015_05
Patent number
US09029411B2

Reaction notes

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