Potassium Carbonate → HCID 66905520, compound

HRID 2040961Notes

Reaction equation

HRID 2040961 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[NH:12]1[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>O.C(O)C>[Cl:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([N:12]3[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13]3)[S:3][C:4]=2[CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 771762,6-DichlorobenzothiazoleHCID 2733874(3S)-pyrrolidin-3-ol

Product 1

HCID 66905520HCID 66905520, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
150 °C

Procedure

A stirred mixture of 2,6-dichlorobenzo[d]thiazole (CAS #3622-23-9, 0.314 g, 3.00 mmol), (S)-pyrrolidin-3-ol (0.314 g, 3.60 mmol), and potassium carbonate (1.24 g, 9.00 mmol) in water/ethanol (10 mL/8 mL) was heated at 150° C. under microwave irradiation for 5 minutes. The reaction mixture was cooled to room temperature then partitioned between dichloromethane and saturated aqueous sodium carbonate. The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to give a crude solid that was purified by crystallization from ethyl acetate/hexane. Crystals were collected by filtration, then dried under vacuum to provide (S)-1-(6-chlorobenzo[d]thiazol-2-yl)pyrrolidin-3-ol. 1H NMR (300 MHz, CD3OD) δ ppm 2.04-2.14 (m, 1H), 2.16-2.29 (m, 1H), 3.48-3.55 (m, 1H), 3.59-3.75 (m, 3H), 4.54-4.59 (m, 1H), 7.26 (dd, J=2, 8 Hz, 1H), 7.40 (d, J=8 Hz, 1H), 7.67 (d, J=2 Hz, 1H); MS (DCI/NH3) m/z 255 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthen partitioned between dichloromethane and saturated aqueous sodium carbonate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto give a crude solid that
  7. customwas purified by crystallization from ethyl acetate/hexane
  8. filtrationCrystals were collected by filtration
  9. customdried under vacuum

Sources & evidence

ORD record
ord-3a8f28ed82a84d2c8f8c1dc5624366e6
Source dataset
uspto-grants-2013_11
Patent number
US08580968B2

Reaction notes

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