Dimethylformamide → HCID 178489250, compound

HRID 1012935Notes

Reaction equation

HRID 1012935 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([OH:14])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl[C:17]1[S:18][C:19]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[C:20]=2[N:21]=1.[H-].[Na+].CN(C=O)C>C1COCC1.O>[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:9][CH2:10][C@H:11]([O:14][C:17]2[S:18][C:19]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[C:20]=3[N:21]=2)[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 20498622-Chloro-4-methoxy-1,3-benzothiazoleHCID 178418329HCID 178418329, compound

Product 1

HCID 178489250HCID 178489250, compoundYield 26.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

trans-(4-hydroxy-cyclohexyl)-carbamic acid tert-butyl ester (2.15 g, 10 mmol) and 2-chloro-4-methoxybenzothiazole (1.99 g, 10 mmol) were dissolved in THF (50 ml) and cooled to 0° C. At this temperature, NaH dispersion (960 mg, 2.2 eq) was added portionwise and the mixture was heated at 60° C. for 2 h. DMF (20 ml) was added and heating was continued for 1 h. The mixture was poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over MgSO4 and concentrated under reduced pressure. Purification by chromatograpy on SiO2 (hex/EtOAc 4:1, 2:1) gave 1 g (26%) of a beige solid.

Workup

  1. temperaturethe mixture was heated at 60° C. for 2 h
  2. temperatureheating
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customPurification by chromatograpy on SiO2 (hex/EtOAc 4:1, 2:1)

Sources & evidence

ORD record
ord-f3d906c1599f4e0ba093f0c45b4adfdf
Source dataset
uspto-grants-2011_07
Patent number
US07981886B2

Reaction notes

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