3-Amino-6-chloro-2-hydroxy-benzenesulfonamide → HCID 20608798, compound

HRID 432614Notes

Reaction equation

HRID 432614 reaction equation
[NH2:1][C:2]1[C:3]([OH:13])=[C:4]([S:9]([NH2:12])(=[O:11])=[O:10])[C:5]([Cl:8])=[CH:6][CH:7]=1.[CH2:14]([O:21][C@H:22]1[CH2:27][CH2:26][CH2:25][CH2:24][C@@H:23]1[N:28]=[C:29]=[O:30])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O>[NH2:12][S:9]([C:4]1[C:3]([OH:13])=[C:2]([NH:1][C:29]([NH:28][C@H:23]2[CH2:24][CH2:25][CH2:26][CH2:27][C@@H:22]2[O:21][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:30])[CH:7]=[CH:6][C:5]=1[Cl:8])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 113680593-Amino-6-chloro-2-hydroxy-benzenesulfonamideHCID 11863574(1S,2S)-2-BENZYLOXYCYCLOHEXYL ISOCYANATE

Product 1

HCID 20608798HCID 20608798, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-amino-6-chloro-2-hydroxybenzenesulfonamide (109 mg, 0.49 mmol) and the crude (1S,2S)-(−)-2-benzyloxycyclohexyl isocynate in 2 mL of N,N-dimethyl-formamide was stirred at room temperature for 20 hours. Purification upon Gilson HPLC, eluting with acetonitrile/water (10/90, v/v to 90/10, v/v, over 10 min), gave the desired product (60 mg, 27% two steps). LC-MS (m/z) 454.0 (M+).

Workup

  1. customPurification upon Gilson HPLC
  2. washeluting with acetonitrile/water (10/90, v/v to 90/10

Sources & evidence

ORD record
ord-ca9db99b16354ee3bcb9f2edc4c45e44
Source dataset
uspto-grants-2003_12
Patent number
US06664259B2

Reaction notes

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