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4-Cyclopropyl-6-methoxy-1,3,5-triazin-2-amine → N-(4-cyclopropyl-6-methoxy-1,3,5-triazin-2-yl)-N'-(2-difluoromethoxybenzenesulfonyl)urea

HRID 462349
Notes
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Reaction equation

HRID 462349 reaction equation
[F:1][CH:2]([F:16])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]=[C:14]=[O:15])(=[O:12])=[O:11].[NH2:17][C:18]1[N:23]=[C:22]([CH:24]2[CH2:26][CH2:25]2)[N:21]=[C:20]([O:27][CH3:28])[N:19]=1>C(Cl)Cl>[CH:24]1([C:22]2[N:21]=[C:20]([O:27][CH3:28])[N:19]=[C:18]([NH:17][C:14]([NH:13][S:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[O:3][CH:2]([F:1])[F:16])(=[O:12])=[O:11])=[O:15])[N:23]=2)[CH2:26][CH2:25]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 27265914-Cyclopropyl-6-methoxy-1,3,5-triazin-2-amineHCID 110969602-Difluoromethoxybenzenesulfonylisocyanate

Product 1

HCID 23311733N-(4-cyclopropyl-6-methoxy-1,3,5-triazin-2-yl)-N'-(2-difluoromethoxybenzenesulfonyl)urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.75 g of 2-difluoromethoxybenzenesulfonylisocyanate are added to a solution of 2.5 g of 2-amino-4-cyclopropyl-6-methoxy-1,3,5-triazine in 15 ml of methylene chloride, and the mixture is stirred for 70 hours at room temperature. It is then concentrated by evaporation, and 25 ml of ether are added to the residue. A crystalline precipitate occurs, which is filtered off. The yield is 4.7 g of the above urea, which melts at 121°-124° C.

Workup

  1. concentrationIt is then concentrated by evaporation, and 25 ml of ether
  2. additionare added to the residue
  3. filtrationwhich is filtered off

Sources & evidence

ORD record
ord-bc504985791d44a9ad4ba009ee180b02
Source dataset
uspto-grants-1985_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04515626

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes