1,2-Dichloroethane → HCID 59129191, compound

HRID 468435Notes

Reaction equation

HRID 468435 reaction equation
[CH3:1][C:2]([C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([N+:16]([O-:18])=[O:17])=[CH:11][CH:10]=2)([CH3:6])[C:3](O)=[O:4].C(Cl)CCl.C1C=CC2N(O)N=[N:29]C=2C=1.[Cl-].[NH4+]>C(#N)C.CCN(CC)CC.O>[CH3:1][C:2]([C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([N+:16]([O-:18])=[O:17])=[CH:11][CH:10]=2)([CH3:6])[C:3]([NH2:29])=[O:4]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 59129178HCID 59129178, compound

Product 1

HCID 59129191HCID 59129191, compoundYield 86,956.5%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

2-Methyl-2-(5-nitro-1H-indol-2-yl)-propanoic acid (4.12 g, 16.6 mmol) was dissolved in acetonitrile (80 mL). EDC (3.80 g, 0.020 mmol), HOBt (2.70 g, 0.020 mmol), Et3N (6.9 mL, 0.050 mmol) and ammonium chloride (1.34 g, 0.025 mmol) were added and the mixture was stirred overnight at room temperature. Water was added and the mixture was extracted with ethylacetate. Combined organic phases were washed with brine, dried over magnesium sulfate and dried to give 2-methyl-2-(5-nitro-1H-indol-2-yl)propanamide (4.3 g, 99%).

Workup

  1. extractionthe mixture was extracted with ethylacetate
  2. washCombined organic phases were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customdried

Sources & evidence

ORD record
ord-074d2dc6eded4d4188d5ccbc6656616c
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

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