3-(Trifluoromethyl)benzoyl chloride → HCID 71621926, compound

HRID 871023Notes

Reaction equation

HRID 871023 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[CH:8]=2)[C:3]=1[C:14]([NH2:16])=[O:15].C(N(CC)C(C)C)(C)C.[F:26][C:27]([F:38])([F:37])[C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31](Cl)=[O:32]>C(Cl)Cl>[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:31](=[O:32])[C:30]3[CH:34]=[CH:35][CH:36]=[C:28]([C:27]([F:26])([F:37])[F:38])[CH:29]=3)[CH:8]=2)[C:3]=1[C:14]([NH2:16])=[O:15]

Participants

5

Reactant 3

HCID 752573-(Trifluoromethyl)benzoyl chloride2×HCID 81531DiisopropylethylamineHCID 86689233HCID 86689233, compound

Product 1

HCID 71621926HCID 71621926, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-amino-3-(3-aminophenyl)isothiazole-4-carboxamide (13 mg, 0.056 mmol) and N,N-diisopropylethylamine (0.029 mL, 0.17 mmol) in 1.0 mL CH2Cl2 at room temperature was added 3-(trifluoromethyl)benzoyl chloride (0.008 mL, 0.056 mmol) and the reaction stirred at room temperature. After 1 hour, additional 3-(trifluoromethyl)benzoyl chloride (0.0015 mL) was added, then again at 2 hours (0.002 mL) and 3 hours (0.0015 mL). After 4 hours the reaction was evaporated, and then treated to an aqueous Na2CO3 and EtOAc workup to yield a light yellow solid. The solid was precipitated from EtOAc/hexane to give the title compound as an off-white solid (16 mg, 68%).

Workup

  1. waitagain at 2 hours (0.002 mL) and 3 hours (0.0015 mL)
  2. customAfter 4 hours the reaction was evaporated
  3. additiontreated to an aqueous Na2CO3 and EtOAc workup
  4. customto yield a light yellow solid
  5. customThe solid was precipitated from EtOAc/hexane

Sources & evidence

ORD record
ord-34330f53ccb54148969987e7d49ff692
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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