Diethyl Ether → HCID 19866494, compound

HRID 1199404Notes

Reaction equation

HRID 1199404 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[S:18][C:17]2[N:16]3[C:19]([CH3:22])=[N:20][N:21]=[C:15]3[CH2:14][N:13]=[C:12]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])[C:11]=2[CH:10]=1.C(OCCCCCCCC1SC2N3C(C)=NN=C3CN=C(C3C=CC=CC=3Cl)C=2C=1)(=O)C.CCOCC>C(Cl)Cl>[CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[S:18][C:17]2[N:16]3[C:19]([CH3:22])=[N:20][N:21]=[C:15]3[CH2:14][N:13]=[C:12]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])[C:11]=2[CH:10]=1)=[O:1]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 19866457HCID 19866457, compoundHCID 19866468HCID 19866468, compound

Product 1

HCID 19866494HCID 19866494, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.1 g (0.005 mol) of 2-(7-hydroxyheptyl)-4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a]-[1,4]diazepine (prepared, for example, from the compound of Example 4 by alkaline saponification) dissolved in 5 ml of methylene chloride are added dropwise to 1.5 g (0.0075 mol) of pyridinechlorochromate in 20 ml of methylene chloride, the resulting mixture is stirred for a further 90 minutes at ambient temperature and 50 of ether are added to the solution. The black resinous oil precipitated is thoroughly extracted several times with ether, the ether solutions are combined, suction filtered over Kieselguhr, the filtrate is evaporated down and the residue is chromatrographed on silica gel with methylene chloride/methanol (9:1) as eluant. 0.6 g (yield 29% of theory) of the aldehyde are obtained as a colourless oil.

Workup

  1. customThe black resinous oil precipitated
  2. filtrationsuction filtered over Kieselguhr
  3. customthe filtrate is evaporated down

Sources & evidence

ORD record
ord-0185a491f2fc46f9934ecf30a2688d45
Source dataset
uspto-grants-1990_02
Patent number
US04900729

Reaction notes

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