Pentyl nitrite → HCID 18793861, compound

HRID 1003961Notes

Reaction equation

HRID 1003961 reaction equation
N(OCCCCC)=O.N[C:10]1[S:11][CH:12]=[C:13]([C:15](=[O:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:14]=1>O1CCCC1>[O:21]=[C:15]([C:13]1[N:14]=[CH:10][S:11][CH:12]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 10026Pentyl nitriteHCID 4356513Ethyl 2-(2-Amino-4-thiazolyl)-2-oxoacetate

Product 1

HCID 18793861HCID 18793861, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of amyl nitrite (5.4 ml) in tetrahydrofuran (45 ml) was added dropwise to a stirred solution of ethyl 2-amino-4-thiazoleglyoxylate (4.00 g) (Aldrich) in tetrahydrofuran (25 ml) at 60° C. When the addition was complete (1 h) the mixture was stirred at 60° C. for a further 2 h. The solvent was evaporated and the residue partitioned between ethyl acetate and sodium bicarbonate solution. The organic phase was washed with water and brine, dried over magnesium sulphate and evaporated. The product (2.54 g) was isolated by column chromatography of the residue using gradient elution (Kieselgel: 2:1 to 1:1 hexane:ethyl acetate). νmax (CHCl3)/cm-1 1737 and 1696. δ (250 MHz, CDCl3), 1.42 (3H, t, J 7.11), 4.46 (2H, q, J 7.22), 8.84 (1H, J 1.95), 8.91 (1H, d, J 1.98).

Workup

  1. additionWhen the addition
  2. custom(1 h)
  3. customThe solvent was evaporated
  4. customthe residue partitioned between ethyl acetate and sodium bicarbonate solution
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-75bd4b2757094fb4a33784a4ebe7b8e5
Source dataset
uspto-grants-2000_04
Patent number
US06048852

Reaction notes

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