4-(Chloromethyl)benzoyl chloride → HCID 59737342, compound

HRID 1013523Notes

Reaction equation

HRID 1013523 reaction equation
[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[NH2:12][C:13]1[CH:18]=[C:17]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)[CH:16]=[CH:15][C:14]=1[NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28].CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>C1COCC1>[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:12][C:13]2[CH:18]=[C:17]([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)[CH:16]=[CH:15][C:14]=2[NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 701364-(Chloromethyl)benzoyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate

Product 1

HCID 59737342HCID 59737342, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-(chloromethyl)benzoyl chloride (2 g, 10.58 mmol) was dissolved in THF (20 mL) and a solution of tert-butyl [2-amino-4-(2-thienyl)phenyl]carbamate (3.38 g, 11.64 mmol) and DIPEA (2.033 mL, 11.64 mmol) in THF (50 mL) was added dropwise at room temperature. After stirring for 1 hour, saturated NaHCO3 was added and the products extracted into EtOAc (×2). The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The residue was triturated in EtOAc to give tert-butyl [2-{[4-(chloromethyl)benzoyl]amino}-4-(2-thienyl)phenyl]carbamate as a beige powder.

Workup

  1. extractionthe products extracted into EtOAc (×2)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated in EtOAc

Sources & evidence

ORD record
ord-51787b1a334949449df88820f5cf8682
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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