Bromine → HCID 178510531, compound

HRID 1993821Notes

Reaction equation

HRID 1993821 reaction equation
[C:1]([CH:3]([C:7](=[S:25])[NH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=2[Cl:23])=[C:11]([F:24])[CH:10]=1)[C:4]([NH2:6])=[O:5])#[N:2].BrBr>C(OCC)(=O)C>[Cl:23][C:17]1[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:16]=1[O:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:7]2[S:25][N:6]=[C:4]([OH:5])[C:3]=2[C:1]#[N:2])=[CH:10][C:11]=1[F:24]

Participants

4

Reactant 2

HCID 24408BromineHCID 597977082-Cyano-2-[4-(2,5-dichloro-phenoxy)-3-fluoro-phenylthiocarbamoyl]-acetamide

Product 1

HCID 178510531HCID 178510531, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

2-Cyano-2-[4-(2,5-dichloro-phenoxy)-3-fluoro-phenylthiocarbamoyl]-acetamide (1.6 g, 4 mmol) was dissolved in anhydrous ethyl acetate (60 ml) and a solution of bromine (0.2 ml, 4 mmol) in anhydrous ethyl acetate (10 ml) was added dropwise into the mixture with stirring at room temperature. After addition, the reaction mixture was stirred for another 3 hours. The precipitate was filtered and the solid was washed with ethyl ether and suspended in a saturated sodium bicarbonate with stirring for 10 min. The solid was filtered, then washed with water and dried in vacuo to afford a white powder.

Workup

  1. additionAfter addition
  2. stirringthe reaction mixture was stirred for another 3 hours
  3. filtrationThe precipitate was filtered
  4. washthe solid was washed with ethyl ether
  5. stirringwith stirring for 10 min
  6. filtrationThe solid was filtered
  7. washwashed with water
  8. customdried in vacuo
  9. customto afford a white powder

Sources & evidence

ORD record
ord-7d752b218a7a4891947964a1a7ef3a59
Source dataset
uspto-grants-2010_01
Patent number
US07652047B2

Reaction notes

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