Chlorosulfonic acid → 1-Acetyl-2,3-dihydro-1H-indole-5-sulfonyl chloride

HRID 2300584Notes

Reaction equation

HRID 2300584 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([S:13]([Cl:16])(=[O:15])=[O:14])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(N1CC2C(=CC=CC=2)C1)(=O)C.ClS(O)(=O)=O.[C:34]([N:37]1[C:45]2[C:40](=[CH:41][C:42]([S:46]([Cl:49])(=[O:48])=[O:47])=[CH:43][CH:44]=2)[CH2:39][CH2:38]1)(=[O:36])[CH3:35]>>[C:34]([N:37]1[C:45]2[C:40](=[CH:41][C:42]([S:46]([Cl:49])(=[O:47])=[O:48])=[CH:43][CH:44]=2)[CH2:39][CH2:38]1)(=[O:36])[CH3:35].[C:1]([N:4]1[CH2:5][C:6]2[C:7](=[CH:8][CH:9]=[C:10]([S:13]([Cl:16])(=[O:14])=[O:15])[CH:11]=2)[CH2:12]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 24638Chlorosulfonic acidHCID 100382071-acetyl-2,3-dihydro-1H-indole-6-sulfonyl chlorideHCID 140245961-Acetyl-2,3-dihydro-1H-indole-5-sulfonyl chlorideHCID 154443561-(2,3-dihydro-1H-isoindol-2-yl)ethan-1-one

Product 2

HCID 140245961-Acetyl-2,3-dihydro-1H-indole-5-sulfonyl chlorideHCID 183765402-acetyl-2,3-dihydro-1H-isoindole-5-sulfonyl chloride

Procedure

N-Acetylindoline-5-sulphonyl chloride was prepared by a literature method (A. L. Borrer, E. Chinoporos, M. Filosa, S. R. Herrchen, C. R. Petersen, C. A. Stern, J. Org. Chem. 53, 2047 (1988)) as was N-acetylindoline-6-sulphonyl chloride (P. R. Carlier, M. P. Lockshin, M. P. Filosa, J. Org. Chem. 59, 3232 (1994)). N-Acetylisoindoline-5-sulphonyl chloride was prepared from N-acetylisoindoline and chlorosulphonic acid in analogy to N-acetylindoline-5-sulphonyl chloride.

Sources & evidence

ORD record
ord-805b4d6e54ca4493a6e8c3566cbb6362
Source dataset
uspto-grants-2002_12
Patent number
US06498183B1

Reaction notes

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