Lithium Hydroxide → 1-[2-(3,5-Dimethylphenyl)-1-(5,6,7,8-tetrahydronaphthalen-1-yl)-ethyl]-3-(2-hydroxyethyl)-thiourea

HRID 2039441Notes

Reaction equation

HRID 2039441 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([NH:21][C:22](=[S:30])[NH:23][CH2:24][CH2:25][O:26]C(=O)C)[C:11]2[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[CH:14]=[CH:13][CH:12]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[OH-].[Li+].C(OCC)(=O)C>C1COCC1.O>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([NH:21][C:22]([NH:23][CH2:24][CH2:25][OH:26])=[S:30])[C:11]2[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[CH:14]=[CH:13][CH:12]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 86657463Acetic acid 2-{3-[2-(3,5-dimethyl-phenyl)-1-(5,6,7,8-tetrahydro-naphthalen-1-yl)-ethyl]-thioureido}-ethyl ester

Product 1

HCID 866574621-[2-(3,5-Dimethylphenyl)-1-(5,6,7,8-tetrahydronaphthalen-1-yl)-ethyl]-3-(2-hydroxyethyl)-thiourea

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of acetic acid 2-{3-[2-(3,5-dimethyl-phenyl)-1-(5,6,7,8-tetrahydro-naphthalen-1-yl)-ethyl]-thioureido}-ethyl ester (2.60 g) in THF (30 ml) was added a solution of lithium hydroxide (294 mg) in water (30 ml) and the mixture stirred for 6 hours at room temperature. The reaction mixture was poured into ethyl acetate (300 ml) and washed with potassium carbonate solution (5 wt % in water). The solution was dried over sodium sulphate. Removal of the solvent in vacuo yielded 1-[2-(3,5-dimethylphenyl)-1-(5,6,7,8-tetrahydronaphthalen-1-yl)-ethyl]-3-(2-hydroxyethyl)-thiourea in 2.28 g (97%) yield.

Workup

  1. washwashed with potassium carbonate solution (5 wt % in water)
  2. dry with materialThe solution was dried over sodium sulphate
  3. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-650482deab89404aae2ef2f5ad1adaef
Source dataset
uspto-grants-2013_11
Patent number
US08580710B2

Reaction notes

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