Potassium Carbonate → HCID 59332842, compound

HRID 1879983Notes

Reaction equation

HRID 1879983 reaction equation
[Br:1]Br.[N:3]1[C:8]2[NH:9][CH2:10][CH2:11][CH2:12][O:13][C:7]=2[CH:6]=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[Br:1][C:5]1[CH:4]=[N:3][C:8]2[NH:9][CH2:10][CH2:11][CH2:12][O:13][C:7]=2[CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24408BromineHCID 59332876HCID 59332876, compound

Product 1

HCID 59332842HCID 59332842, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of bromine (960 mg, 6 mmol) in CH2Cl2 (50 mL) was added dropwise at 0° C. to a CH2Cl2 (50 mL) suspension of 6,7,8,9-tetrahydro-5-oxa-1,9-diaza-benzocycloheptene (750 mg, 5 mmol) and solid K2CO3 (1 g). The mixture was stirred for 30 min at 20° C., then the excess bromine was quenched with a saturated solution of aqueous NaHSO3. The basic aqueous phase was separated, extracted with CH2Cl2, the combined organic layers were dried and evaporated to afford the title compound (1.10 g, 96%). 1H NMR (300 MHz, DMSO-d6, 8): 7.78 (d, J=1.8 Hz, 1H), 7.30 (d, J=1.9 Hz, 1H), 6.35 (s, br, 1H), 4.10 (t, J=5.7 Hz, 2H), 3.24 (m, 2H), 1.92 (m, 2H). MS (ESI): m/e 229 and 231 (M+H)+.

Workup

  1. customthe excess bromine was quenched with a saturated solution of aqueous NaHSO3
  2. customThe basic aqueous phase was separated
  3. extractionextracted with CH2Cl2
  4. customthe combined organic layers were dried
  5. customevaporated

Sources & evidence

ORD record
ord-8400310b1cb34243a37519d034643cc0
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

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