Octanoyl chloride → HCID 20070872, compound

HRID 981781Notes

Reaction equation

Cl.[NH2:2][CH2:3][C:4]1[CH:8]=[CH:7][S:6][CH:5]=1.C(N(CC)CC)C.[C:16](Cl)(=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>>[S:6]1[CH:7]=[CH:8][C:4]([CH2:3][NH:2][C:16](=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:5]1

Participants

Reactant 3

HCID 8124Octanoyl chloride

HCID 8471Triethylamine

HCID 16956077Thiophen-3-ylmethyl-ammonium chloride

Product 1

HCID 20070872HCID 20070872, compoundYield 89%

Procedure

Using the same reaction conditions as those of Example 4, 3-(aminomethyl)thiophene hydrochloride (4 mmol), triethylamine (4.4 mmol) and octanoyl chloride (40 mmol) were reacted to give N-(3-thienylmethyl)octanamide (0.85 g, 89%). M.p. 71°-72° C. (Found: C, 65.0; H, 8.4; N. 5.7; S, 13.2. Calculated for C13H21NOS: C, 65.3; H, 8.8; N, 5.9; S, 13.4%); EI m/e Intensity (%): 239 (19, M+), 97 (63, C4H3S.CH2+); δH(CDCl3) 7.03-7.33 (3H, m), 5.60 (1H, br,s), 4.44 (2H, d), 2.19 (2H, t), 1.61 (2H, m), 1.28 (8H, m), 0.87 (3H, t); δC(CDCl3): 14.2, 22.7, 25.8, 29.1, 29.3, 31.8, 36.9, 38.8, 122.3, 126.5, 127.1, 140.0, 173.1 ppm.

Workup

customwere reacted

Sources & evidence

ORD record: ord-184bdaf819244518bfd8905af293c361
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04992559

Reaction notes

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