Chloroacetyl chloride → HCID 86689957, compound

HRID 716850Notes

Reaction equation

HRID 716850 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]([CH2:22][CH2:23][Cl:24])[CH2:19][CH2:20][Cl:21])=[CH:14][CH:13]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.[Cl:25][CH2:26][C:27](Cl)=[O:28]>C1COCC1>[Cl:24][CH2:23][CH2:22][N:18]([CH2:19][CH2:20][Cl:21])[C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:9](=[O:10])[NH:8][C:4]2[CH:3]=[C:2]([NH:1][C:27](=[O:28])[CH2:26][Cl:25])[CH:7]=[CH:6][CH:5]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 86689956HCID 86689956, compound

Product 1

HCID 86689957HCID 86689957, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 46a (3.0 g, 8.0 mmol) in THF (100 mL), chloroacetyl chloride (2.2 g, 20 mmol) in THF (50 mL) was added dropwise at RT and the resulting mixture was stirred at RT for additional 45 minutes. The reaction mixture was evaporated under reduced pressure and the solid residue was triturated with saturated aqueous solution of NaHCO3 and then filtered. The solid was washed successfully with water and hexane, and dried to yield N-(3-(3-(4-(bis(2-chloroethyl)amino)-phenyl)ureido)phenyl)-2-chloroacetamide, 2.8 g (82%); mp 232-233° C. 1H NMR (DMSO-d6) δ: 2.80-2.83 (2H, t, J=5.9 Hz, CH2), 3.68-3.71 (8H, m, CH2), 3.86-3.89 (2H, t, J=5.9 Hz, CH2), 6.70-6.72 (2H, d, J=8.5 Hz, Ar—H), 7.14-7.30 (5H, m, Ar—H), 7.76 (1H, s, Ar—H), 8.46 (1H, brs, NH), 8.73 (1H, brs, NH), 10.04 (1H, brs, NH).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customthe solid residue was triturated with saturated aqueous solution of NaHCO3
  3. filtrationfiltered
  4. washThe solid was washed successfully with water and hexane
  5. customdried

Sources & evidence

ORD record
ord-48975048880243888f8fe917f6d4aef4
Source dataset
uspto-grants-2015_11
Patent number
US09193687B2

Reaction notes

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