Diethylethanolamine → HCID 23294950, compound

HRID 1955280Notes

Reaction equation

HRID 1955280 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1([C:11]([OH:13])=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7]1.O=S(Cl)[Cl:16].[CH2:18]([N:20]([CH2:24][CH3:25])[CH2:21][CH2:22]O)[CH3:19]>C1(C)C=CC=CC=1>[ClH:16].[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1([C:11]([O:13][CH2:19][CH2:18][N:20]([CH2:24][CH3:25])[CH2:21][CH3:22])=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 7497DiethylethanolamineHCID 24386Thionyl ChlorideHCID 232948861-(Thiophen-2-yl)cyclopentane-1-carboxylic acid

Product 1

HCID 23294950HCID 23294950, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-(2-thienyl)cyclopentanecarboxylic acid (3.1 mmol), prepared in Example 94 above, was refluxed with SOCl2 (0.6 mL) in 4 mL toluene. After 4 h, the reaction mixture was evaporated and the residue was dissolved in toluene. 2-Diethylaminoethanol (9.3 mmol) was added and the mixture was stirred at room temperature overnight. The crude was chromatographed on silica gel using toluene-Et3N 95:5 as eluent. The yield was 0.79 g (76%); mp 122-123° C.; 1H NMR (CDCl3) δ 1.28 (t, 6H), 1.75 (m, 4H), 2.13 (m, 2H), 2.50 (m, 2H), 2.92 (m, 4H), 3.22 (m, 2H), 4.60 (t, 2H), 6.95 (dd, 2H), 7.19 (dd, 1H), 12.4 (br, 1H). Anal. (C16H25NO2S.HCl) C, H, N.

Workup

  1. customthe reaction mixture was evaporated
  2. dissolutionthe residue was dissolved in toluene
  3. customThe crude was chromatographed on silica gel

Sources & evidence

ORD record
ord-700f3ed977064ce99c5c43741645a68d
Source dataset
uspto-grants-2000_09
Patent number
US06124354

Reaction notes

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