N-Ethoxymethanamine → HCID 14011488, compound

HRID 246991Notes

Reaction equation

HRID 246991 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:6][C:5]2[CH:7]=[C:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]=[C:19]=[O:20])=[CH:14][CH:13]=3)[CH:9]=[CH:10][C:4]=2[O:3]1.[CH3:22][NH:23][O:24][CH2:25][CH3:26]>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:21])[CH2:6][C:5]2[CH:7]=[C:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19]([N:23]([O:24][CH2:25][CH3:26])[CH3:22])=[O:20])=[CH:14][CH:13]=3)[CH:9]=[CH:10][C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 14895678N-EthoxymethanamineHCID 20161048HCID 20161048, compound

Product 1

HCID 14011488HCID 14011488, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

1.8 g of 4-(2,3-dihydro-2,2-dimethyl-5-benzofuranyloxy)phenyl isocyanate was dissolved in 20 ml of toluene, and 2.0 g of N-methyl-O-ethylhydroxylamine dissolved in 5 ml of toluene, was dropwise added thereto over a period of 20 minutes at room temperature. The mixture was stirred at room temperature for 2 hours, and then the solvent was distilled off. The residue was purified by silica gel column chromatography by using a solvent mixture of ethyl acetate/n-hexane=1/4 as the developer, to obtain 2.2 g of compound No. 29 as identified in Table 1.

Workup

  1. additionwas dropwise added
  2. distillationthe solvent was distilled off
  3. customThe residue was purified by silica gel column chromatography
  4. additiona solvent mixture of ethyl acetate/n-hexane=1/4 as the developer

Sources & evidence

ORD record
ord-8f23056336404209a1e9e21294f6ca0a
Source dataset
uspto-grants-1987_11
Patent number
US04705554

Reaction notes

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