Diazomethane → HCID 14836267, compound

HRID 703068Notes

Reaction equation

HRID 703068 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[S:6][C:7]([C:18]([OH:20])=[O:19])=[C:8]([CH2:9][N:10]([CH2:12][CH:13]([O:16][CH3:17])[O:14][CH3:15])[CH3:11])[C:4]=2[CH:3]=1.[N+](=[CH2:25])=[N-]>C(Cl)Cl.O1CCCC1.C(OCC)C>[CH3:25][O:19][C:18]([C:7]1[S:6][C:5]2[CH:21]=[CH:22][C:2]([Cl:1])=[CH:3][C:4]=2[C:8]=1[CH2:9][N:10]([CH2:12][CH:13]([O:16][CH3:17])[O:14][CH3:15])[CH3:11])=[O:20]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 14836266HCID 14836266, compound

Product 1

HCID 14836267HCID 14836267, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 5-chloro-3-[N-(2,2-dimethoxyethyl)-N-methyl(aminomethyl)]benzo[b]thiophene-2-carboxylic acid (5.0 g, 14.5 mmol) in methylene chloride-tetrahydrofuran was stirred at 0° C. and treated with excess diazomethane in ethyl ether. The mixture was stirred for 2 hours at 0° C., treated with a stream of argon and concentrated to give 5.0 g (96%) of methyl-5-chloro-3-[N-(2,2-dimethoxyethyl)-N-methyl(aminomethyl)]benzo[b]thiophene-2-carboxylate.

Workup

  1. stirringThe mixture was stirred for 2 hours at 0° C.
  2. additiontreated with a stream of argon
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b04724ead5c64d579e0ee64a96c0cce2
Source dataset
uspto-grants-1991_01
Patent number
US04981848

Reaction notes

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