Triethylamine → HCID 18975624, compound

HRID 2393329Notes

Reaction equation

HRID 2393329 reaction equation
[CH2:1]([NH:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7])[CH3:2].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]=[C:17]=[S:18])=[C:12]([CH3:19])[CH:11]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[S:18])[N:3]([CH2:4][CH2:5][C:6]([OH:8])=[O:7])[CH2:1][CH3:2])=[C:12]([CH3:19])[CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 900213-Chloro-6-isothiocyanatotolueneHCID 12227201HCID 12227201, compound

Product 1

HCID 18975624HCID 18975624, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Ethylaminopropionic acid (19.8 g) was reacted with 4-chloro-2-methylphenylisothiocyanate (20 g), triethylamine (20 g), and methylene chloride (250 mL) according to the procedure described in step 2 of Example 1 to give 12 g of 3-[3-(4-chloro-2-methylphenyl)-1-ethyl-thioureido]propionic acid. The product (12 g) was dissolved in acetone (245 mL). Conc. HCl (5 mL) was added and the mixture was heated at reflux for 18 hours. The reaction mixture was evaporated to dryness. The residue was dissolved in methylene chloride (100 mL), and washed with 1N NaOH. The organic phase was dried over anhydrous magnesium sulfate, then evaporated to dryness. The solid was recrystallized from ethanol. The title compound (8 g) was obtained as a white solid., m.p. 133°-136° C.

Sources & evidence

ORD record
ord-a14f1ca3b07549ada6682576dd54aa71
Source dataset
uspto-grants-1998_09
Patent number
US05807864

Reaction notes

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