Dimethylcarbamoyl Chloride → HCID 15136679, compound

HRID 358974Notes

Reaction equation

HRID 358974 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:6][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:4][C:3]1=[O:13].[CH3:15][N:16]([CH3:20])[C:17](Cl)=[O:18]>N1C=CC=CC=1.C(N(CC)CC)C.C(Cl)Cl>[CH3:1][C:2]1([CH3:14])[CH2:6][N:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:4]=[C:3]1[O:13][C:17](=[O:18])[N:16]([CH3:20])[CH3:15]

Participants

6

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 758614,4-Dimethyl-1-phenyl-3-pyrazolidone

Product 1

HCID 15136679HCID 15136679, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4,4-dimethyl-1-phenyl-3-pyrazolidinone (1.90 g) in a mixture of 25 mL pyridine and 4 mL triethylamine at 0° C. is added N,N-dimethylcarbamoyl chloride (1.37 mL). The reaction mixture is stirred at room temperature for 16 hours. The reaction mixture is diluted with methylene chloride (100 mL) and washed with 10% aqueous hydrochloric acid (200 mL). The organic layer is dried (MgSO4), filtered and evaporated. Chromatography on silica gel gave a light yellow solid. Recrystallization from ethanol gave 1.80 g (73%) of pale yellow crystals. (MP-99°-100° C.; Analysis: C-64.26%, H-7.19%, N-16.04%; H1NMR-δ 7.6-2H,t; δ 7.35-2H,d; δ 7.15-2H,t; δ 4.1-2H,s; δ 3.4-3H,s; δ 3.3-3H,s; δ 1.7-6H,s).

Workup

  1. washwashed with 10% aqueous hydrochloric acid (200 mL)
  2. dry with materialThe organic layer is dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customChromatography on silica gel gave a light yellow solid
  6. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-7e2066bb775a46348bf37b877e75e3fe
Source dataset
uspto-grants-1991_03
Patent number
US04999368

Reaction notes

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