Triethylamine → HCID 21092795, compound

HRID 1348960Notes

Reaction equation

HRID 1348960 reaction equation
Cl.Cl.[CH2:3]([O:5][C:6](=[O:12])[CH2:7][NH:8][CH2:9][CH2:10][NH2:11])[CH3:4].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[S:24][C:23]([S:25](Cl)(=[O:27])=[O:26])=[N:22][N:21]=2)=[CH:16][CH:15]=1.C(N(CC)CC)C>ClCCl>[CH2:3]([O:5][C:6](=[O:12])[CH2:7][NH:8][CH2:9][CH2:10][NH:11][S:25]([C:23]1[S:24][C:20]([C:17]2[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=2)=[N:21][N:22]=1)(=[O:26])=[O:27])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21092752HCID 21092752, compoundHCID 74889816N-beta-Aminoethyl-gly-oet 2hcl

Product 1

HCID 21092795HCID 21092795, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-aminoethyl)-glycine ethyl ester 2HCl (1.4 g, 6.4 mmol), prepared as described by Will (D. W. Will et al., Tetrahedron, 1995, 51, 12069.), in dichloromethane (50 mL) was added 5-(4-chlorophenyl)-1,3,4-thiadiazole-2-sulfonyl chloride (1.5 g, 5.1 mmol) at 0° C. Then triethylamine (2.7 mL) was slowly added. The resulting reaction mixture was stirred for additional 2 h. at room temperature and washed with water (30 mL). The organic layer was dried over MgSO4 and filtered. The filtrate was concentrated, followed by column chromatography to give the title compound (1.1 g, 2.7 mmol, 53%) as a solid. 1H NMR (500 MHz; DMSO-d6) δ 8.08 (d, 2H), 7.66 (d, 2H), 4.03 (q, 2H), 3.26 (s, 2H), 3.15 (t, 2H), 2.64 (t, 2H), 1.14 (t, 3H).

Workup

  1. customThe resulting reaction mixture
  2. washwashed with water (30 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3c057fd76cb4467ebbadb895608b9802
Source dataset
uspto-grants-2007_05
Patent number
US07211668B2

Reaction notes

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