Triethylamine → Cyclosulfamuron

HRID 1085390Notes

Reaction equation

HRID 1085390 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.Cl[S:13]([N:16]=[C:17]=[O:18])(=[O:15])=[O:14].[CH:19]1([C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[NH2:30])=[O:23])[CH2:21][CH2:20]1.C(N(CC)CC)C>C(Cl)Cl>[CH:19]1([C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[NH:30][S:13]([NH:16][C:17]([NH:1][C:2]2[N:3]=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([O:8][CH3:9])[N:7]=2)=[O:18])(=[O:15])=[O:14])=[O:23])[CH2:20][CH2:21]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 10931741(2-Aminophenyl)(cyclopropyl)methanone

Product 1

HCID 6451137Cyclosulfamuron

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.78 g (0.0114 mole) of 2-amino-4,6-dimethoxypyrimidine in 50 mL of methylene chloride is cooled to 0.5° C. in an ice bath and 1.0 mL (1.62 g, 0.114 mole) of chlorosulfonyl isocyanate then added to the solution. The resulting mixture is stirred for 30 minutes and a solution of 2.66 g o-aminophenyl cyclopropyl ketone (70% real, 0.0114) and 2.6 mL triethylamine (0.0187 mole) in 50 mL of methylene chloride then slowly added to the mixture. The resulting solution is stirred at ambient temperature overnight (18 hours).

Workup

  1. stirringThe resulting solution is stirred at ambient temperature overnight (18 hours)

Sources & evidence

ORD record
ord-18d85f2360974f0eb021becd2f653f5a
Source dataset
uspto-grants-1991_04
Patent number
US05009699

Reaction notes

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