Ammonium Hydroxide → HCID 86737973, compound

HRID 895017Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([NH2:5])=[O:4].[CH3:8][C:9]1[C:19]2[CH2:18][CH2:17][NH:16][CH2:15][CH:14]([C:20]3[CH:25]=[CH:24][C:23]([S:26](O)(=[O:28])=[O:27])=[CH:22][CH:21]=3)[C:13]=2[CH:12]=[C:11]2[O:30][CH2:31][O:32][C:10]=12.S(Cl)(Cl)(=O)=O.S(Cl)(Cl)=O.C[N:43](C)C=O.[OH-].[NH4+]>>[F:1][C:2]([F:7])([F:6])[C:3]([NH2:5])=[O:4].[CH3:8][C:9]1[C:19]2[CH2:18][CH2:17][NH:16][CH2:15][CH:14]([C:20]3[CH:25]=[CH:24][C:23]([S:26](=[O:28])(=[O:27])[NH2:43])=[CH:22][CH:21]=3)[C:13]=2[CH:12]=[C:11]2[O:30][CH2:31][O:32][C:10]=12

Participants

Reactant 4

HCID 14923Ammonium Hydroxide

HCID 24648Sulfuryl chloride

HCID 71351191Sulfurous dichloride--N,N-dimethylformamide (1/1)

HCID 86737974HCID 86737974, compound

Product 1

HCID 86737973HCID 86737973, compound

Procedure

The sulfonic acid (750 mg) is converted to the sulfonyl chloride using thionyl chloride/dimethylformamide then reacted without purification with an excess of ammonium hydroxide to give 6-methyl-7,8-methylenedioxy-1-(p-sulfamylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine trifluoroacetamide. Alkaline hydrolysis of the acetamide (500 mg) and boron tribromide treatment of the residue in the cold gives the desired 6-methyl-7,8-dihydroxy-1-(p-sulfamylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride.

Sources & evidence

ORD record: ord-6afe0b7691a84e5d981eb05041d60dad
Source dataset: uspto-grants-1981_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04285938

Reaction notes

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