Benzenesulfonyl isocyanate, 2-chloro- → HCID 13469506, compound

HRID 615822Notes

Reaction equation

HRID 615822 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][CH2:10][O:11][CH3:12])[CH:5]=[C:4]([CH3:13])[N:3]=1.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([N:24]=[C:25]=[O:26])(=[O:23])=[O:22]>C(Cl)Cl>[CH3:12][O:11][CH2:10][CH2:9][O:8][C:6]1[CH:5]=[C:4]([CH3:13])[N:3]=[C:2]([NH:1][C:25]([NH:24][S:21]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[Cl:14])(=[O:22])=[O:23])=[O:26])[N:7]=1

Participants

4

Reactant 2

HCID 174071Benzenesulfonyl isocyanate, 2-chloro-HCID 3777900HCID 3777900, compound

Product 1

HCID 13469506HCID 13469506, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dry stirred solution of 18.3 parts of 2-amino-4-(2-methoxyethoxy)-6-methylpyrimidine in 300 parts of methylene chloride at ambient temperature and pressure was added 22 parts of 2-chlorobenzenesulfonylisocyanate. The mixture was stirred for 2 hours and then the methylene chloride was removed under reduced pressure. The resulting solid was triturated with 1-chlorobutane and filtered to yield 35 parts of N-[[4-(2-methoxyethoxy)-6-methylpyrimidine-2-yl]aminocarbonyl]-2-chlorobenzenesulfonamide, m.p. 130°-140° C. The product showed characteristic absorption bands in the infrared spectrum.

Workup

  1. customthe methylene chloride was removed under reduced pressure
  2. customThe resulting solid was triturated with 1-chlorobutane
  3. filtrationfiltered

Sources & evidence

ORD record
ord-cb0103c0c8f448cdb5e28c5a73d2bf9c
Source dataset
uspto-grants-1985_02
Patent number
US04501607

Reaction notes

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