Sodium Bicarbonate → HCID 13188510, compound

HRID 1285280Notes

Reaction equation

HRID 1285280 reaction equation
C(=O)(O)[O-].[Na+].[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:23])[CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1.[CH3:24][N:25]([O:29][CH3:30])[C:26](Cl)=[O:27]>O1CCCC1>[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:23])[CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([NH:22][C:26]([N:25]([CH3:24])[O:29][CH3:30])=[O:27])=[CH:20][CH:21]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734926N-methoxy-N-methylcarbamoyl chlorideHCID 27682673-(4-aminophenyl)-1-(4-methylphenyl)propan-1-one

Product 1

HCID 13188510HCID 13188510, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

15.3 g of sodium bicarbonate were added to a solution, in 250 ml of tetrahydrofuran, of 36 g of the 1-(4-methylphenyl)-3-(4-aminophenyl)-n-propan-1-one prepared as described in Example A, and 18.5 g of N-methyl-N-methoxycarbamyl chloride were added dropwise at 10°-15° C., while cooling with ice. The mixture was stirred for 6 hours at 25° C., after which it was filtered and the filtrate was evaporated down under reduced pressure. The oil obtained crystallized after trituration with diisopropyl ether, and 38.5 g (79% of theory) of product of melting point 73°-74° C. were obtained.

Workup

  1. customprepared
  2. additionwere added dropwise at 10°-15° C.
  3. temperaturewhile cooling with ice
  4. filtrationafter which it was filtered
  5. customthe filtrate was evaporated down under reduced pressure
  6. customThe oil obtained
  7. customcrystallized after trituration with diisopropyl ether, and 38.5 g (79% of theory) of product of melting point 73°-74° C.
  8. customwere obtained

Sources & evidence

ORD record
ord-42ed6b25d09844688b4e9a818d46be7e
Source dataset
uspto-grants-1986_01
Patent number
US04566900

Reaction notes

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