Sulfuric Acid → HCID 131714302, compound

HRID 484981Notes

Reaction equation

S(=O)(O)[O-].[Na+].[NH:6]([C:10]1[CH:15]=[C:14](S(O)=O)[CH:13]=[CH:12][C:11]=1[O:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26](S(O)=O)=[CH:25][C:24]=1[NH:32]C(C)=O)C(C)=O.[CH2:36]1[O:38][CH2:37]1.N(C1C=C(S(CCO)(=O)=O)C=CC=1OCCOC1C=CC(S(CCO)(=O)=O)=CC=1NC(C)=O)[C:40]([CH3:42])=[O:41].S(=O)(=O)(O)O>>[NH2:32][C:24]1[CH:25]=[C:26]([CH2:42][CH2:40][OH:41])[CH:27]=[CH:28][C:23]=1[O:22][CH2:21][CH2:20][O:19][C:11]1[CH:12]=[CH:13][C:14]([CH2:37][CH2:36][OH:38])=[CH:15][C:10]=1[NH2:6]

Participants

Reactant 5

HCID 1118Sulfuric Acid

HCID 6354Ethylene Oxide

HCID 23665763Sodium Bisulfite

HCID 86061236HCID 86061236, compound

HCID 131714303HCID 131714303, compound

Product 1

HCID 131714302HCID 131714302, compound

Procedure

328.4 parts of ethylene glycol bis-(2-acetaminophenyl)ether are reacted in accordance with Example 1 with 1,100 parts of chlorosulfonic acid and 250 parts of thionyl chloride to give ethylene glycol bis-(2-acetamino-4-chlorosulfonylphenyl)ether. After its isolation, this compound is reduced in the method described in Example 1 by means of 572 parts of 40% strength aqueous sodium bisulfite to ethylene glycol bis-(2-acetamino-4-sulfinophenyl)ether and, analogously to the method in Example 1, the resulting bis-sulfinic acid is converted, by means of 540 parts of ethylene oxide, into ethylene glycol bis-(2-acetamino-4-hydroxyethylsulfonylphenyl)ether. The crude product, as detailed in Example 1, is deacetylated by means of 1,500 parts of 5% strength aqueous sulfuric acid and ethylene glycol bis-(2-amino-4-β-hydroxyethylphenyl)ether is formed. This product, after drying, melts at 144°-146° C.

Sources & evidence

ORD record: ord-63a26a76145d4561b5b8400e194e5833
Source dataset: uspto-grants-1985_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04534908

Reaction notes

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