Benzenesulfonyl isocyanate, 2-chloro- → HCID 13206551, compound

HRID 1980444Notes

Reaction equation

HRID 1980444 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]=[C:12]=[O:13])(=[O:10])=[O:9].[NH2:14][C:15]1[N:24]=[C:23]([N:25]([CH3:27])[CH3:26])[C:22]2[C:17](=[N:18][CH:19]=[CH:20][N:21]=2)[N:16]=1>C(#N)C>[CH3:26][N:25]([CH3:27])[C:23]1[C:22]2[C:17](=[N:18][CH:19]=[CH:20][N:21]=2)[N:16]=[C:15]([NH:14][C:12]([NH:11][S:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])(=[O:10])=[O:9])=[O:13])[N:24]=1

Participants

4

Reactant 2

HCID 174071Benzenesulfonyl isocyanate, 2-chloro-HCID 20401649HCID 20401649, compound

Product 1

HCID 13206551HCID 13206551, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.5 g (0.0070 mol) of 2-chlorophenylsulfonyl isocyanate were added to a suspension of 1.3 g (0.0068 mol) of 2-amino-4-dimethylaminopteridine in 40 ml of acetonitrile and the mixture was stirred at reflux for 4 hours. The mixture was vacuum filtered and the filtrate was concentrated by evaporation. The residue was treated with acetone to obtain 2.05 g (74% of theory) of N-(4-dimethylaminopteridine-2-yl)-N'-(2-chlorophenylsulfonyl)-urea in the form of light yellow crystals melting at 232° C.

Workup

  1. temperatureat reflux for 4 hours
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated by evaporation
  4. additionThe residue was treated with acetone

Sources & evidence

ORD record
ord-34e1786913064bbcb4c303d588a660a2
Source dataset
uspto-grants-1985_04
Patent number
US04509972

Reaction notes

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