Benzenesulfonyl chloride → 9-Benzenesulfonyl-4-bromo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene

HRID 388284Notes

Reaction equation

HRID 388284 reaction equation
BrC1C2OCCNC=2C=C(C)C=1.[Br:13][C:14]1[C:24]2[O:23][CH2:22][CH2:21][CH2:20][NH:19][C:18]=2[CH:17]=[CH:16][CH:15]=1.[C:25]1([S:31](Cl)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[C:25]1([S:31]([N:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([Br:13])[C:24]=3[O:23][CH2:22][CH2:21][CH2:20]2)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 22557236HCID 22557236, compound2×HCID 225572458-Bromo-6-methyl-3,4-dihydro-2h-1,4-benzoxazine

Product 1

HCID 225572949-Benzenesulfonyl-4-bromo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene

Procedure

In another variation of the above procedure, 8-bromo-6-methyl-3,4-dihydro-2H-benzo[1,4]oxazine was replaced with 4-bromo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene (obtained by reduction of 4-bromo-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one, which in turn was prepared by reaction of 2-amino-6-bromophenol with 3-chloropropionyl chloride as described by Combs et al.; J. Med. Chem.; 33; 380-386 1990). Reaction of 4-bromo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene with benzenesulfonyl chloride yielded 9-benzenesulfonyl-4-bromo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene as a white solid, MS: M+=336.

Sources & evidence

ORD record
ord-1d6ba1511e36455f99f6348a72a1a0fa
Source dataset
uspto-grants-2013_02
Patent number
US08377931B2

Reaction notes

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