Diethylamine → HCID 22311901, compound

HRID 966475Notes

Reaction equation

HRID 966475 reaction equation
[Cl:1][CH:2]([CH2:6][CH3:7])[C:3](Cl)=[O:4].[CH2:8]([NH:10][CH2:11][CH3:12])[CH3:9]>C(Cl)Cl.[OH-].[Na+]>[Cl:1][CH:2]([CH2:6][CH3:7])[C:3]([N:10]([CH2:11][CH3:12])[CH2:8][CH3:9])=[O:4]

Participants

5

Reactant 2

HCID 8021DiethylamineHCID 1390532-Chlorobutanoyl chloride

Product 1

HCID 22311901HCID 22311901, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

Following the procedure of Kem K. M.; Nguyen N. V.; Cross D. J. J. Org. Chem. 1981;46:5188 for the preparation of chloroacetamides, a solution of 2-chlorobutyryl chloride (61.91 mmol, 8.73 g, Lancaster) in 28 mL of CH2Cl2 was added to diethylamine (56.28 mol, 4.12 g, Aldrich) in a mixture of CH2Cl2 (56 mL) and NaOH (56 mL, 20% aqueous) at −25° C. to furnish 2-chloro-N,N-diethyl-butyramide (7.23 g, 72%). 1HNMR (400 MHz, CDCl3) δ 0.98 (t, J=7.33 Hz, 3H, CH2CH3), 1.12 (t, J=7.08 Hz, 3H, CH2CH3), 1.19-1.23 (m, 3H, CH2CH3), 1.89-2.00 (m, 1H, CH2CH3), 2.03-2.14 (m, 1H, CH2CH3), 3.22-3.38 (m, 2H, NCH2CH3), 3.41-3.52 (m, 2H, NCH2CH3), 4.26 (t, J=7.08 Hz, 1H, CHCl); MS(APCI+): m/z 177.9 (M+1), 179.9 (M+3).

Sources & evidence

ORD record
ord-73d76e0adc1947ff9afa3c9cd71a9c31
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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