Diisopropylethylamine → HCID 86640687, compound

HRID 2176097Notes

Reaction equation

HRID 2176097 reaction equation
[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][C:40](Cl)=[O:41])=[CH:35][CH:34]=1>CN(C)C=O>[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][C:40]([N:9]([C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[N:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:41])=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 906924-Chlorophenylacetyl chlorideHCID 6426133HCID 6426133, compound

Product 1

HCID 86640687HCID 86640687, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-chilled solution of 1-(diphenylmethylene)-2-p-tolylhydrazine (270 mg, 0.94 mmol; Example 36A) and N,N-diisopropyl-N-ethylamine (120 mg, 0.94 mmol; Aldrich) in N,N-dimethylformamide (2.0 mL) was added 2-(4-chlorophenyl)acetyl chloride (178 mg, 0.94 mmol; Alfa Aesar). After 10 minutes the ice bath was removed and the reaction mixture was stirred at room temperature overnight (18 hours). The reaction mixture was diluted with water (10 mL) and extracted with dichloromethane (2×20 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the crude product, which was carried on to the next step without further purification: LC/MS m/z 439 (M+H)+.

Workup

  1. customAfter 10 minutes the ice bath was removed
  2. additionThe reaction mixture was diluted with water (10 mL)
  3. extractionextracted with dichloromethane (2×20 mL)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6e8cfbcdfe0c4bbbb1be51224c9d94bd
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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