Diethyl Sulfate → HCID 20530992, compound

HRID 1759511Notes

Reaction equation

HRID 1759511 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:16].[C:17](OC(=O)C)(=[O:19])[CH3:18].S(OCC)(O[CH2:28][CH3:29])(=O)=O.C(Cl)C>C(O)(=O)C.[OH-].[Na+]>[NH:1]([C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([OH:15])(=[O:13])=[O:14])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:16][CH2:28][CH3:29])[C:17]([CH3:18])=[O:19]

Participants

7

Reactant 4

HCID 6163Diethyl SulfateHCID 6337ChloroethaneHCID 7918Acetic AnhydrideHCID 1458041-Amino-2-naphthol-6-sulfonic acid

Product 1

HCID 20530992HCID 20530992, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 14798Sodium HydroxideSolvent

Procedure

According to Examples 2 and 3 of German Democratic Republic Pat. No. 9,728, 1-amino-2-ethoxy-naphthalene-6-sulphonic acid, is obtained by a procedure in which, in a first stage, 1-acetamino-2-hydroxy-naphthalene-6-sulphonic acid is prepared from 1-amino-2-hydroxy-naphthalene-6-sulphonic acid by reaction with acetic anhydride in dilute acetic acid, this intermediate product is etherified, in a second stage, with diethyl sulphate or with ethyl chloride in aqueous-alcoholic sodium hydroxide solution to give 1-acetamino-2-ethoxy-naphthalene-6-sulphonic acid, and, finally, this intermediate product is deacetylated, without intermediate isolation, by heating with aqueous sodium hydroxide solution to give 1-amino-2-ethoxy-naphthalene-6-sulphonic acid.

Sources & evidence

ORD record
ord-387f3205b27849f8b30fe898c781f3aa
Source dataset
uspto-grants-1982_07
Patent number
US04341719

Reaction notes

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