HCID 68459548, compound → HCID 11653128, compound

HRID 2356978Notes

Reaction equation

HRID 2356978 reaction equation
Cl.[C:2]1([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15]([CH2:21][NH2:22])[CH2:16][CH2:17][O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:23]([C:25]#[N:26])[K]>O>[C:2]1([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15]([CH2:21][NH:22][C:25]([NH2:26])=[O:23])[CH2:16][CH2:17][O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 68459548HCID 68459548, compoundHCID 178418250HCID 178418250, compound

Product 1

HCID 11653128HCID 11653128, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

C-(7-Benzenesulfonyl-chroman-4-yl)-methylamine HCl salt (75 mg, 0.22 mmol) was dissolved in 8 mL water and KOCN (36 mg, 0.44 mmol) was added. The reaction mixture was stirred at 100° C. for 30 minutes., then cooled, partitioned between EtOAc and water, and dried over MgSO4. After concentration, the product was precipitated from Et2O/hexanes. After formation of the HCl salt, 24 mg (32%) of (7-Benzenesulfonyl-chroman-4-ylmethyl)-urea was collected. MS: 347 (M+H)+.

Workup

  1. temperature, then cooled
  2. custompartitioned between EtOAc and water
  3. dry with materialdried over MgSO4
  4. concentrationAfter concentration
  5. customthe product was precipitated from Et2O/hexanes
  6. customAfter formation of the HCl salt, 24 mg (32%) of (7-Benzenesulfonyl-chroman-4-ylmethyl)-urea was collected

Sources & evidence

ORD record
ord-46e05f436573424a87f045d56186cf89
Source dataset
uspto-grants-2010_07
Patent number
US07759389B2

Reaction notes

Loading…