Chloroacetyl chloride → HCID 58124891, compound

HRID 1971745Notes

Reaction equation

HRID 1971745 reaction equation
[C:1]([N:5]1[CH2:31][CH2:30][CH2:29][CH2:28][C:8]2[C:9]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[C:10]3[C:19]4[CH:18]=[C:17]([NH2:20])[C:16]([O:21][CH3:22])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:32])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:40][CH2:41][C:42](Cl)=[O:43]>C(Cl)Cl.O>[Cl:40][CH2:41][C:42]([NH:20][C:17]1[C:16]([O:21][CH3:22])=[CH:15][C:14]2[CH2:13][CH2:12][N:11]3[C:7]4[C:6](=[O:32])[N:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:31][CH2:30][CH2:29][CH2:28][C:8]=4[C:9]([C:23]4[S:24][CH:25]=[CH:26][CH:27]=4)=[C:10]3[C:19]=2[CH:18]=1)=[O:43]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 58124894HCID 58124894, compound

Product 1

HCID 58124891HCID 58124891, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 365 mg of 20b and 160 ul of triethylamine in 1 ml of CH2Cl2 was added at 0° C. 90 ul of chloroacetylchloride in ½ ml of CH2Cl2. The reaction was stirred for 15 min, and then diluted with water and extracted with ethyl acetate. The extract was washed several times with water, and then dried and concentrated. The residue was treated with diethylether, to provide, after decantation of the supernatant and drying 390 mg of light grey solid 22a; Rf (heptane/ethyl acetate) 0.50 (Rf 20b: 0.60). NMR (CDCl3) δ 8.73 (bs, 1, NH), 7.42, 7.18, and 6.96 (3×m, 3, thienyl-H), 6.72 and 8.12 (2×s, 2, Ar—H), 4.62 and 3.88 (2×bm, 2, CH2), 4.08 (s, 2, CH2Cl), 3.87 (s, 3, OCH3), 3.90 and 3.50 (2×bm, 2, CH2), 2.90+3.10 (2×b.m, 2, CH2), 2.52 (b.m, 2, CH2), 1.60-2.0 (b.m, 4, 2×CH2), 1.57 (s, 9, tertC4H9).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed several times with water
  3. customdried
  4. concentrationconcentrated
  5. additionThe residue was treated with diethylether
  6. customto provide
  7. dry with materialafter decantation of the supernatant and drying 390 mg of light grey solid 22a

Sources & evidence

ORD record
ord-769f6d2c345840c3b1212c488ee6df1b
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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