Chlorosuccinimide → HCID 86718878, compound

HRID 528810Notes

Reaction equation

C(OC([NH:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][C:13]([S:19]([OH:22])(=[O:21])=[O:20])=[CH:14]2)=O)(C)(C)C.[Cl:23]N1C(=O)CCC1=O>>[NH2:8][C:9]1[CH:18]=[CH:17][C:16]([Cl:23])=[C:15]2[C:10]=1[CH:11]=[CH:12][C:13]([S:19]([OH:22])(=[O:21])=[O:20])=[CH:14]2

Participants

Reactant 2

HCID 31398Chlorosuccinimide

HCID 86718879HCID 86718879, compound2×

Product 1

HCID 86718878HCID 86718878, compoundYield 100.1%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 31B, 5-(tert-butoxycarbonylamino)naphthalene-2-sulfonic acid (Intermediate 31A, 3.70 g, 11.44 mmol) and N-chlorosuccinimide (1.60 g, 12.01 mmol) were converted to the title compound (2.95 g, 90%). MS(ESI+) m/z 275.1 (M+NH4)+.

Sources & evidence

ORD record: ord-27330be751fd4b908fb1086cdfbbad1f
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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