Triethylamine → HCID 10513072, compound

HRID 864956Notes

Reaction equation

HRID 864956 reaction equation
[C:1]([CH2:3][O:4][C:5]1[C:6]2[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=2[S:8][C:9]=1[C:10](O)=[O:11])#[N:2].CCN(CC)CC.[H][H]>C1COCC1>[O:4]1[C:5]2[C:6]3[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=3[S:8][C:9]=2[C:10](=[O:11])[NH:2][CH2:1][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21459890HCID 21459890, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10513072HCID 10513072, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the methyl ester of 3-(cyanomethoxy)benzo[b]thiophene-2-carboxylic acid (405 mg, 1.64 mmols) [J. Hetero. Chem., 12:1037 (1975)], 0.5 mL of Et3N and 0.50 g of RaCo in 50 mL of THF is heated at 100° C. under 1200 psi of hydrogen. The reaction mixture is concentrated in vacuo. Column chromatography eluting with a gradient of 1:1 hexane:ethyl acetate to all ethyl acetate provides 2,3-dihydro-[1]benzothieno[2,3-f]1,4-oxazepin-5(4H)-one in 55% yield; mp 244°-245° C.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. washColumn chromatography eluting with a gradient of 1:1 hexane

Sources & evidence

ORD record
ord-4a1cbd7e06db4220b230e454c674105c
Source dataset
uspto-grants-1996_10
Patent number
US05565446

Reaction notes

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