1,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine → HCID 53881320, compound

HRID 840928Notes

Reaction equation

HRID 840928 reaction equation
[C:1]1([C:7]2[CH:15]=[C:14]3[C:10]([CH2:11][C:12](=[O:16])[NH:13]3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O[CH:22](OC(C)(C)C)[N:23]([CH3:25])[CH3:24])(C)(C)C>CN(C=O)C>[CH3:22][N:23]([CH:25]=[C:11]1[C:10]2[C:14](=[CH:15][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:8][CH:9]=2)[NH:13][C:12]1=[O:16])[CH3:24]

Participants

4

Reactant 2

HCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 105363846-Phenyl-1,3-dihydro-indol-2-one

Product 1

HCID 53881320HCID 53881320, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Phenyloxindole (0.053 mg, 0.25 mmol) and dimethylformamide di-t-butylacetal (0.08 mL, 0.32 mmol) were combined and dissolved in DMF. The reaction mixture was stirred at room temperature for 4 hours. The volatiles were removed in vacuo and the resulting residue was triturated with diethyl ether. The solids were collected by filtration (50 mg, 75% yield). ). 1H NMR 400 MHz (DMSO-d6) mixture of E and Z isomers: δ10.09 (s, 1H); 10.02 (s, 1H); 7.59-7.51 (m, 4H); 7.45-7.22 (m, 10H); 7.10-7.05 (m, 2H); 6.98 (s, 1H); 6.91 (s, 1H); 3.29 (s, 12H).

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe resulting residue was triturated with diethyl ether
  3. filtrationThe solids were collected by filtration (50 mg, 75% yield)
  4. addition1H NMR 400 MHz (DMSO-d6) mixture of E and Z isomers

Sources & evidence

ORD record
ord-4b4814401bd74388909f851ec7645917
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Reaction notes

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