Cyclohexane → HCID 59823518, compound

HRID 1426866Notes

Reaction equation

HRID 1426866 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([O:8][C:9]2[C:15]([CH3:16])=[CH:14][C:12]([NH2:13])=[C:11]([CH3:17])[CH:10]=2)[S:5][C:6]=1[Cl:7].CO[CH:20](OC)[N:21]([CH3:24])[CH2:22][CH3:23].C1CCCCC1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:3]=[C:4]([O:8][C:9]2[C:15]([CH3:16])=[CH:14][C:12]([N:13]=[CH:20][N:21]([CH2:22][CH3:23])[CH3:24])=[C:11]([CH3:17])[CH:10]=2)[S:5][C:6]=1[Cl:7]

Participants

6

Reactant 4

HCID 8078CyclohexaneHCID 8857Ethyl AcetateHCID 23017846N-(dimethoxymethyl)-N-methylethanamineHCID 59823517HCID 59823517, compound

Product 1

HCID 59823518HCID 59823518, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

To a mixture of 2.0 g (6.9 mmol) of 4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline in 2.5 ml toluene a solution of 9.7 mmol of N-(dimethoxymethyl)-N-methylethanamine (60% in methanol) was added. The reaction mixture was stirred for 16 hrs at 105° C. The reaction mixture was concentrated in vacuo. Column chromatographie (gradient: cyclohexane->ethyl acetate) yielded 2.4 g (6.7 mmol) 97% of N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide; log P (pH 2.3)=2.04

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-bab67df0b2bd461099e63b32ddab594d
Source dataset
uspto-grants-2015_01
Patent number
US08933107B2

Reaction notes

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