Benzoyl isothiocyanate → HCID 86724267, compound

HRID 873724Notes

Reaction equation

HRID 873724 reaction equation
[NH2:1][C:2]1([C:15]([F:19])([F:18])[CH2:16][OH:17])[C:11]2([CH2:13][CH2:12]2)[CH2:10][O:9][C:8]2[C:3]1=[CH:4][C:5]([Br:14])=[CH:6][CH:7]=2.[C:20]([N:28]=[C:29]=[S:30])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CC(C)=O>[Br:14][C:5]1[CH:4]=[C:3]2[C:8](=[CH:7][CH:6]=1)[O:9][CH2:10][C:11]1([CH2:13][CH2:12]1)[C:2]2([NH:1][C:29]([NH:28][C:20](=[O:27])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[S:30])[C:15]([F:19])([F:18])[CH2:16][OH:17]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 86724268HCID 86724268, compound

Product 1

HCID 86724267HCID 86724267, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Under ice cooling, to a solution of 2-(4-amino-6-bromo-4H-spiro[chromene-3,1′-cyclopropan]-4-yl)-2,2-difluoroethanol (2.24 g, 6.46 mmol) in acetone (45 mL) was added benzoyl isothiocyanate (1.16 g, 7.10 mmol), and the mixture was stirred for 2 hours at room temperature and stirred for 13 hours at 40° C. After concentration, the residue was purified by silica gel chromatography (EtOAc/hexane=1:99-30:70) followed by purification using silica gel chromatography (NH-silicagel, EtOH/CHCl3=0:100-10:90) to give N-{[6-bromo-4-(1,1-difluoro-2-hydroxyethyl)-4H-spiro[chromene-3,1′-cyclopropan]-4-yl]carbamothioyl}benzamide (684 mg).

Workup

  1. stirringstirred for 13 hours at 40° C
  2. concentrationAfter concentration
  3. customthe residue was purified by silica gel chromatography (EtOAc/hexane=1:99-30:70)
  4. customfollowed by purification

Sources & evidence

ORD record
ord-3cf868c3168c47ba963094342fe65908
Source dataset
uspto-grants-2015_03
Patent number
US08975415B2

Reaction notes

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