Water → 2-(4-Carbomethoxyphenyl)-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-thiazole

HRID 346288

Reaction equation

HRID 346288 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](=[S:11])[NH2:10])=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2].Cl[CH2:15][C:16]([C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[C:24]([CH3:29])([CH3:28])[CH2:23][CH2:22][C:21]2([CH3:31])[CH3:30])=O.O>C(O)(C)C.N1C=CC=CC=1>[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]2[S:11][CH:15]=[C:16]([C:18]3[CH:27]=[CH:26][C:25]4[C:24]([CH3:29])([CH3:28])[CH2:23][CH2:22][C:21]([CH3:31])([CH3:30])[C:20]=4[CH:19]=3)[N:10]=2)=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2]

Participants

6

Reactant 3

HCID 962WaterHCID 11401319Methyl 4-carbamothioylbenzoateHCID 147265332-Chloro-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)ethanone

Product 1

HCID 147265422-(4-Carbomethoxyphenyl)-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-thiazole

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 3776IsopropanolSolvent

Procedure

3.2 g (16.5 moles) of 4-carbomethoxybe-nzothiamide and 4.2 g (16 millimoles) of 6-chloroacetyl-1,2,3,4-tetrahydro-1,1,,4,4-tetramethylnaphthalene (for preparation see Example 28) in 40 ml of isopropanol were refluxed for 1 hour with the addition of 2 drops of pyridine. The mixture was cooled, water was added and the crystals formed were filtered off under suction. Recrystallization from isopropanol and a trace of water gave 3.0 g of the title compound of melting point 138°-140° C.

Workup

  1. temperatureThe mixture was cooled
  2. customthe crystals formed
  3. filtrationwere filtered off under suction
  4. customRecrystallization from isopropanol

Sources & evidence

ORD record
ord-5f1b4dfbe40a4283a968cffce353375e
Source dataset
uspto-grants-1991_10
Patent number
US05061705

Linked notes

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