m-Chloroperbenzoic acid → HCID 21242883, compound

HRID 621442Notes

Reaction equation

[C:1]([N:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[C:12]([O:17][CH3:18])[C:13]([S:15][CH3:16])=[CH:14][C:7]=2[CH2:6][CH2:5]1)(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:27])C=1>>[C:1]([N:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[C:12]([O:17][CH3:18])[C:13]([S:15]([CH3:16])=[O:27])=[CH:14][C:7]=2[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 70297m-Chloroperbenzoic acid

HCID 13853354HCID 13853354, compound

Product 1

HCID 21242883HCID 21242883, compound

Procedure

Following the general procedure of Example 4 Method B, 3-acetyl-8-methoxy-7-methylthio-2,3,4,5-tetrahydro-1H-3-benzazepine is reacted with one equivalent of 3-chloroperbenzoic acid to give 3-acetyl-8-methoxy-7-methylsulfinyl-2,3,4,5-tetrahydro-1H-3-benzazepine. Following the procedure of Example 4, 3-acetyl-8-methoxy-7-methylsulfinyl-2,3,4,5-tetrahydro-1H-3-benzazepine is reacted with 3N hydrochloric acid to give 8-methoxy-7-methylsulfinyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride. This methoxy compound is treated with pyridine hydrochloride to give 8-hydroxy-7-methylsulfinyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride.

Sources & evidence

ORD record: ord-981f649871114a28be585af3d79659a5
Source dataset: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04824839

Reaction notes

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