HCID 19779484, compound → HCID 19779480, compound

HRID 2082073Notes

Reaction equation

HRID 2082073 reaction equation
C(N(CC)CCCS(C1C=CC(N)=CC=1)(=NC(OCC1C=CC=CC=1)=O)=[O:8])C.[CH2:29]([N:31]([CH2:56][CH3:57])[CH2:32][CH2:33][CH2:34][S:35]([C:48]1[CH:53]=[CH:52][C:51]([NH:54][OH:55])=[CH:50][CH:49]=1)(=[N:37][C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])=[O:36])[CH3:30]>>[CH2:56]([N:31]([CH2:29][CH3:30])[CH2:32][CH2:33][CH2:34][S:35]([C:48]1[CH:49]=[CH:50][C:51]([N+:54]([O-:8])=[O:55])=[CH:52][CH:53]=1)(=[N:37][C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])=[O:36])[CH3:57]

Participants

3

Reactant 2

HCID 19779484HCID 19779484, compoundHCID 19779492HCID 19779492, compound

Product 1

HCID 19779480HCID 19779480, compound

Procedure

A solution of a 3:1 mixture of 4-[S-[3-(diethylamino)propyl]-N-[(phenylmethoxy)carbonyl]sulfonimidoyl]benzeneamine and S-[3-(diethylamino)propyl]-S-[4-(hydroxyamino)phenyl]-N-[(phenylmethoxy)carbonyl]sulfoximine obtained through an incomplete reduction of S-[3-(diethylamino)propyl)-S-(4-nitrophenyl)-N-[(phenylmethoxy)carbonyl]sulfoximine (4.2 g, ~10 mmol) was dissolved in a pyridine (42 mL)-methylene chloride (12 mL) mixture. The resulting solution was cooled in an ice/water bath, and methanesulfonyl chloride (1.2 g, 10 mmol) was added. The reaction mixture was allowed to come to ambient temperature and was stirred for 4 h. The reaction mixture was then added to 200 mL of diethyl ether. The ethereal solution was decanted from the insoluble residue. The residue was triturated with an additional 100 mL of diethyl ether, and the ethereal solution was decanted and discarded. The residue was dried in vacuo to give 3.0 g of a gum that was chromatographed (flash, silica gel, 95:5-90:10 methylene chloride-methanol) to give 0.7 g of product (15%). A 200 mg sample was dissolved in ethanol and treated with ethereal HCl. The solid that formed was recrystallized from ethanol. This solid was triturated with ethyl acetate and then recrystallized from ethanol. The resulting solid was recrystallized from an ethanol/diethyl ether mixture to give 0.02 g of off-white solid, mp 76°-78° C.

Sources & evidence

ORD record
ord-5ef7f587b03143d2ac465643edad7f9d
Source dataset
uspto-grants-1993_02
Patent number
US05187189

Reaction notes

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