Carbon Tetrachloride → HCID 58137792, compound

HRID 2189447Notes

Reaction equation

HRID 2189447 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:30]=[CH:29][C:13]([C:14]([NH:16][NH:17][C:18]4C=[CH:27][CH:26]=[CH:25][C:19]=4[C:20]([O:22][CH2:23][CH3:24])=[O:21])=O)=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1.C(Cl)(Cl)(Cl)Cl.C([N:41](C(C)C)CC)(C)C.C(P(CC)CC)C>C(Cl)Cl.C1COCC1>[Cl:1][C:2]1[CH:32]=[CH:31][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([C:14]4[N:41]5[CH:27]=[CH:26][CH:25]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:18]5=[N:17][N:16]=4)=[CH:29][CH:30]=3)[S:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 5943Carbon TetrachlorideHCID 27365TriethylphosphineHCID 81531DiisopropylethylamineHCID 86650850HCID 86650850, compound

Product 1

HCID 58137792HCID 58137792, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 2-(2-(4-(6-chlorobenzo[d]thiazol-2-ylamino)benzoyl)hydrazinyl)benzoate (142 mg, 0.3 mmol) in a mixed solvent of CCl4 (0.6 mL), THF (0.8 mL) and CH2Cl2 (1.2 mL) cooled to 0° C. was added diisopropylethylamine (392 mg, 3 mmol) under argon atmosphere and then triethylphosphine (179 mg, 1.52 mmol). The mixture was stirred at 0° C. for 45 min, and then quenched with water (2.5 mL). The resulting precipitate was isolated by filtration and air dried to yield the title compound as a brown solid (108 mg). The filtrate was concentrated in vacuo to yield additional product (15 mg) (total 123 mg, 90% yield). HPLC/MS (Method C): retention time=2.21 min, [M+H]+=450.3.

Workup

  1. customquenched with water (2.5 mL)
  2. customThe resulting precipitate was isolated by filtration and air
  3. customdried

Sources & evidence

ORD record
ord-4fa03dc8d59c4012ba6fed150cef99b9
Source dataset
uspto-grants-2012_12
Patent number
US08324241B2

Reaction notes

Loading…