Phenyl chloroformate → Phenyl (4-cyano-3-(4-nitrophenyl)isothiazol-5-yl)carbamate

HRID 870990Notes

Reaction equation

HRID 870990 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=2)[C:3]=1[C:16]#[N:17].C(N(CC)C(C)C)(C)C.Cl[C:28]([O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:29]>CN(C1C=CN=CC=1)C.ClCCCl>[C:16]([C:3]1[C:4]([C:7]2[CH:8]=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=2)=[N:5][S:6][C:2]=1[NH:1][C:28](=[O:29])[O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)#[N:17]

Participants

6

Reactant 3

HCID 15891Phenyl chloroformateHCID 81531DiisopropylethylamineHCID 690551855-Amino-3-(4-nitrophenyl)isothiazole-4-carbonitrile

Product 1

HCID 86689217Phenyl (4-cyano-3-(4-nitrophenyl)isothiazol-5-yl)carbamate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 5-amino-3-(4-nitrophenyl)isothiazole-4-carbonitrile (394 mg, 1.60 mmol), N,N-diisopropylethylamine (0.836 mL, 4.8 mmol), and catalytic DMAP in 20 mL 1,2-dichloroethane at rt was added phenyl chloroformate (0.301 mL, 2.40 mmol) drop wise over 1 minute. The reaction mixture was stirred at rt for 22 hours, then added directly to a dry packed silica gel column eluting with CHCl3, then gradient 10% to 50% EtOAc in CHCl3. The title compound was obtained as a beige solid (131 mg, 22%) and used as is for the next step.

Workup

  1. additionadded directly to a dry
  2. washeluting with CHCl3

Sources & evidence

ORD record
ord-0970a099307646e493f685dff008ef19
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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