Diethylcarbamoyl chloride → HCID 15675450, compound

HRID 974004Notes

Reaction equation

HRID 974004 reaction equation
[CH2:1]([NH:11][OH:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C(N(CC)CC)C.[CH2:20]([N:22]([CH2:26][CH3:27])[C:23](Cl)=[O:24])[CH3:21]>O1CCCC1.CN(C)C1C=CN=CC=1>[CH2:20]([N:22]([CH2:26][CH3:27])[C:23]([N:11]([OH:12])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[O:24])[CH3:21]

Participants

6

Reactant 3

HCID 6916Diethylcarbamoyl chlorideHCID 8471TriethylamineHCID 33377N-Decylhydroxylamine

Product 1

HCID 15675450HCID 15675450, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of N-decylhydroxylamine (2.60 g, 15.0 mmol) and triethylamine (2.3 ml) in tetrahydrofuran (hereinafter THF) (30 ml) at 0° C. was added dropwise N,N-diethylcarbamyl chloride (1.92 ml). After two hours, 4-(dimethylamino)pyridine (1.3 g) was added. After 18 hours, the reaction mixture was quenched with 1N hydrochloric acid (hereinafter HCl), extracted with hexane, and the organic solution was dried over MgSO4, filtered and evaporated. Trituration of the residue with hexane at -30° C. gave the title compound as a while solid (3.1 g, mp 35°-37° C.).

Workup

  1. waitAfter 18 hours
  2. customthe reaction mixture was quenched with 1N hydrochloric acid (hereinafter HCl),
  3. extractionextracted with hexane
  4. dry with materialthe organic solution was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-b0abdd8a4f7f401a8c93cf17065e6d9b
Source dataset
uspto-grants-1991_11
Patent number
US05066658

Reaction notes

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