Butylamine → HCID 54044452, compound

HRID 650586Notes

Reaction equation

HRID 650586 reaction equation
[C:1]([CH:4]=[C:5]1[C:13]2[CH:12]=[CH:11][S:10][C:9]=2[CH2:8][CH2:7][CH2:6]1)([OH:3])=O.[CH2:14]([NH2:18])[CH2:15][CH2:16][CH3:17].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(=O)([O-])O.[Na+]>CCOC(C)=O.CN(C)C=O>[CH2:14]([NH:18][C:1]([CH:4]=[C:5]1[C:13]2[CH:12]=[CH:11][S:10][C:9]=2[CH2:8][CH2:7][CH2:6]1)=[O:3])[CH2:15][CH2:16][CH3:17]

Participants

8

Reactant 5

HCID 8007ButylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53667594HCID 53667594, compound

Product 1

HCID 54044452HCID 54044452, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-carboxymethylidene-4,5,6,7-tetrahydrobenzo[b]thiophene (0.50 g), n-butylamine (0.28 ml), 1-hydroxybenzotriazole (0.43 g) and dimethylformamide (DMF) (5 ml) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.54 g). The reaction mixture was stirred at r.t. for 5 hours and poured into a mixture of AcOEt and a saturated aqueous solution of sodium hydrogen carbonate (NaHCO3). The separated organic layer was washed with water and brine, and dried over MgSO4, and evaporated to give 4-(N-butylcarbamoyl)methylidene-4,5,6,7-tetrahydrobenzo[b]thiophene (0.60 g).

Workup

  1. washThe separated organic layer was washed with water and brine
  2. dry with materialdried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-da127d28c45949a5b43ced459c61fe48
Source dataset
uspto-grants-2001_08
Patent number
US06274619B1

Reaction notes

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