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Dimethylformamide → 1-(2-Aminobenzothiazol-6-yl)-3-(4-chloro-3-trifluoromethylphenyl)urea

HRID 2108901
Notes
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Reaction equation

HRID 2108901 reaction equation
CC(OC([NH:8][C:9]1[S:13][C:12]2[CH:14]=[C:15]([NH2:18])[CH:16]=[CH:17][C:11]=2[N:10]=1)=O)(C)C.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]=[C:27]=[O:28])=[CH:22][C:21]=1[C:29]([F:32])([F:31])[F:30].CN(C)C=O.FC(F)(F)C(O)=O>ClCCl.O>[NH2:8][C:9]1[S:13][C:12]2[CH:14]=[C:15]([NH:18][C:27]([NH:26][C:23]3[CH:24]=[CH:25][C:20]([Cl:19])=[C:21]([C:29]([F:31])([F:30])[F:32])[CH:22]=3)=[O:28])[CH:16]=[CH:17][C:11]=2[N:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6422Trifluoroacetic acidHCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 58305681HCID 58305681, compound2×

Product 1

HCID 231325021-(2-Aminobenzothiazol-6-yl)-3-(4-chloro-3-trifluoromethylphenyl)urea

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-aminobenzothiazol-2-yl tert-butyl carbamate (Intermediate 4, 0.796 g, 3.0 mmol), 4-chloro-3-(trifluoromethyl)phenyl isocyanate (0.731 g, 3.3 mmol) and dimethylformamide (80 mL) was stirred overnight at r.t. Water was added, the resulting precipitate was filtered off, washed thoroughly with water and dried. The so obtained material was suspended in dichloromethane (15 mL) and trifluoroacetic acid (15 mL) was added. After stirring for 1.5 h at r.t., the volatiles were removed in vacuo and dimethylformamide (20 mL) was added to the residue. The solution was neutralised by adding saturated sodium hydrogencarbonate solution. Water was added and the resulting precipitate was filtered off, washed with water and dried (grey solid, 0.999 g, 2.58 mmol, 86%). LC/ESI-MS: m/z=387 [M(35Cl)+H]+; m/z=385 [M(35Cl)−H]−; Rt=3.54 min.

Workup

  1. filtrationthe resulting precipitate was filtered off
  2. washwashed thoroughly with water
  3. customdried
  4. customThe so obtained material
  5. stirringAfter stirring for 1.5 h at r.t.
  6. customthe volatiles were removed in vacuo and dimethylformamide (20 mL)
  7. additionwas added to the residue
  8. additionby adding saturated sodium hydrogencarbonate solution
  9. additionWater was added
  10. filtrationthe resulting precipitate was filtered off
  11. washwashed with water
  12. customdried (grey solid, 0.999 g, 2.58 mmol, 86%)

Sources & evidence

ORD record
ord-9017e9b89ecb442c987e96d5bae09430
Source dataset
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07514460B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes