Methyl iodide → HCID 12848219, compound

HRID 1732926Notes

Reaction equation

HRID 1732926 reaction equation
[CH:1]1[S:2][CH:3]=[C:4]2[C:10]=1[C:9](=[O:11])[NH:8][C:7]1[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=1[O:5]2.[CH3:16][C:17]1[CH:18]=[CH:19][C:20]2[O:26][C:25]3=CSC=[C:24]3[C:23](=O)[NH:22][C:21]=2[CH:31]=1.[CH3:32][O-:33].[Na+].CI>C(O)C>[CH3:16][N:8]1[C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=2[O:5][C:4]2=[CH:3][S:2][CH:1]=[C:10]2[C:9]1=[O:11].[CH3:16][C:17]1[C:18]2[C:19]([C:32](=[O:33])[SH:2]([CH3:1])[CH:3]=2)=[C:20]2[O:26][CH2:25][CH:24]=[CH:23][N:22]=[C:21]2[CH:31]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 12581860HCID 12581860, compoundHCID 12703381HCID 12703381, compound

Product 2

HCID 12848219HCID 12848219, compoundHCID 178421795HCID 178421795, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The starting material, thieno[3,4-b][1,5]benzoxazepin-10(9H)-one (I) or 7-methyl-thieno[3,4-b][1,5]benzoxazepin-10(9H)-one (II) in ethanol is treated with sodium methoxide and methyl iodide and extracted with methylene chloride to yield 9-methyl-thieno[3,4-b][1,5]benzoxazepin-10(9H)-one (III) and 7,9-dimethyl-thieno[3,4][1,5]benzoxazepin-10(9H)-one (IV) respectively. The above compounds III and IV are refluxed with 5 N sodium hydroxide for 16 hours, diluted with water, adjusted to pH 4-5 with hydrochloric acid and extracted with methylene chloride. The base compounds thus obtained are dissolved in ether and treated with alcoholic hydrochloric acid to give the corresponding 4-(o-methylaminophenoxy)-3-thiophenecarboxylic acid hydrochloride (V) and 4-(2-methylamino-p-tolyloxy)-3-thiophenecarboxylic acid hydrochloride (VI) compounds.

Workup

  1. extractionextracted with methylene chloride

Sources & evidence

ORD record
ord-671e9dca96ea48ce834f8a30b81c9120
Source dataset
uspto-grants-1980_12
Patent number
US04239898

Reaction notes

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