Diisopropylethylamine → 1-(2,3-Dihydro-2-methylbenzofuran-7-yl)-4-methoxy-4-methylsemicarbazide

HRID 1583752Notes

Reaction equation

HRID 1583752 reaction equation
[CH3:1][O:2][N:3]([CH3:7])[C:4](Cl)=[O:5].[NH:8]([C:10]1[C:18]2[O:17][CH:16]([CH3:19])[CH2:15][C:14]=2[CH:13]=[CH:12][CH:11]=1)[NH2:9].C(N(C(C)C)CC)(C)C>C1COCC1>[CH3:19][CH:16]1[CH2:15][C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([NH:8][NH:9][C:4]([N:3]([O:2][CH3:1])[CH3:7])=[O:5])[C:18]=2[O:17]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2734926N-methoxy-N-methylcarbamoyl chlorideHCID 135358277-Hydrazino-2,3dihydro-2-methylbenzofuran

Product 1

HCID 135358281-(2,3-Dihydro-2-methylbenzofuran-7-yl)-4-methoxy-4-methylsemicarbazide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4.9 g of N-methoxy-N-methylcarbamic chloride was added, drop-by-drop (over 5 minutes) to a mixture of 6.6 g of 1D, 125 ml of THF and 5.2 g of N,N-diisopropyl-N-ethylamine, at -10° C. The mixture was stirred for 1 hour at 0° C., and then mixed with ice water. The resulting mixture was extracted with ether, and extract was dried (MgSO4), filtered and the solvent was evaporated, to give 1-(2,3-dihydro-2-methylbenzofuran-7-yl)-4-methoxy-4-methylsemicarbazide (1E), as an amber syrup.

Workup

  1. extractionThe resulting mixture was extracted with ether
  2. extractionextract
  3. dry with materialwas dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2246a9e15f0544cfb92a033e367ce736
Source dataset
uspto-grants-1985_11
Patent number
US04554283

Reaction notes

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