Chloroacetyl chloride → HCID 140620633, compound

HRID 2206287Notes

Reaction equation

HRID 2206287 reaction equation
[NH2:1][C:2]1[O:3][C:4]2[C:9]([CH:10]([C:16]3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([Br:26])[CH:17]=3)[C:11]=1[C:12]([NH:14]O)=[NH:13])=[CH:8][CH:7]=[C:6]1[CH:27]=[CH:28][CH:29]=[CH:30][C:5]=21.C(N(CC)CC)C.[Cl:38][CH2:39][C:40](Cl)=[O:41].[O:43]1CCCC1>O>[NH2:1][C:2]1[O:3][C:4]2[C:9]([C:10]([OH:43])([C:16]3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([Br:26])[CH:17]=3)[C:11]=1[C:12]([NH:14][C:40](=[O:41])[CH2:39][Cl:38])=[NH:13])=[CH:8][CH:7]=[C:6]1[CH:27]=[CH:28][CH:29]=[CH:30][C:5]=21

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 178487567HCID 178487567, compound

Product 1

HCID 140620633HCID 140620633, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Amino-4-(3-bromo-4,5-dimethoxy-phenyl)-N-hydroxy-4H-benzo[h]chromene-3-carboxamidine (21) (118 mg, 0.25 mmol) and triethylamine (35 ml, 0.25 mmol) are taken in 10 ml tetrahydrofuran at −5° C. and is charged with chloroacetyl chloride (23 mg, 0.25 mmol) by drop wise addition under strong stirring. The reaction mixture is then stirred allowing to come to room temperature under LC-MS control and is stirred further at room temperature till the reaction is complete. The reaction mixture is diluted with water to about 50 ml and stirred for 2 h at room temperature. Thus resulting precipitates are separated by filtration, washed well with water and is dried under high vacuum to get solids of the title compound.

Workup

  1. customto come to room temperature under LC-MS control
  2. stirringis stirred further at room temperature till the reaction
  3. stirringstirred for 2 h at room temperature
  4. customThus resulting
  5. customprecipitates
  6. customare separated by filtration
  7. washwashed well with water
  8. customis dried under high vacuum

Sources & evidence

ORD record
ord-d8804f09da3a4abe98221864bfbc92f4
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

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