Methyl iodide → HCID 57855981, compound

HRID 2039629Notes

Reaction equation

HRID 2039629 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([NH2:16])=[C:7]([Cl:15])[CH:8]2[S:12][C:11]([SH:13])=[N:10][CH:9]2[CH:14]=1)=[O:4].CI.[CH3:19]CN(CC)CC>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[C:6]([NH2:16])=[C:7]([Cl:15])[CH:8]2[S:12][C:11]([S:13][CH3:19])=[N:10][CH:9]2[CH:14]=1)=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 178497011HCID 178497011, compound

Product 1

HCID 57855981HCID 57855981, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound is prepared as described in Acta. Chim. Slov. 2002, 49, 871 using the crude 6-amino-7-chloro-2-mercapto-3a,7a-dihydro-benzothiazole-5-carboxylic acid methyl ester as starting material. Methylation is performed with MeI and Et3N in DMF. The 6-amino-7-chloro-2-methylsulfanyl-3a,7a-dihydro-benzothiazole-5-carboxylic acid methyl ester is obtained, after column chromatography purification over silica gel, in 59% over 3 steps from 2,5-diamino-3-chloro-4-(2-trimethylsilanyl-ethylsulfanyl)-benzoic acid methyl ester (step d in example H17); LC/MS: 289/291 (M+1)+.

Workup

  1. customThis compound is prepared

Sources & evidence

ORD record
ord-049f7e1fa101413d9dcb31502c24d1b4
Source dataset
uspto-grants-2013_11
Patent number
US08580785B2

Reaction notes

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