Bicarbonate Ion → HCID 21192588, compound

HRID 1067953Notes

Reaction equation

HRID 1067953 reaction equation
[CH:1]1([N:4]([CH:12]=[C:13]([C:19](OCC)=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]2[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=2)[CH2:3][CH2:2]1.C(=O)(O)[O-]>ClCCl>[CH:1]1([N:4]2[C:5]3[C:6](=[CH:7][C:8]([I:11])=[CH:9][CH:10]=3)[C:19](=[O:20])[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 769Bicarbonate IonHCID 21192534HCID 21192534, compound

Product 1

HCID 21192588HCID 21192588, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a flask containing diethyl 2-[(cyclopropyl-4-iodoanilino)methylene]malonate from Preparation No. 18 (0.22 g) is added polyphosphoric acid (1.4 g). The reaction mixture is capped and heated to 120° C. over 1 hour. After 2 hours at 120° C. the reaction is cooled to room temperature, treated with ice and partioned between dichloromethane and saturated aqueous bicarbonate. The basic aqueous layer is extracted with two additional portions of dichloromethane. The combined organic layers are washed with brine, dried over sodium sulfate and concentrated under reduced pressure to afford 0.19 g of the title compound as a tan solid.

Workup

  1. customfrom Preparation No
  2. customThe reaction mixture is capped
  3. temperatureAfter 2 hours at 120° C. the reaction is cooled to room temperature
  4. additiontreated with ice
  5. extractionThe basic aqueous layer is extracted with two additional portions of dichloromethane
  6. washThe combined organic layers are washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-36d0f91d1ee9424780764bda43c83b45
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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