Dichloromethane → HCID 21833458, compound

HRID 1740846Notes

Reaction equation

HRID 1740846 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:13])[CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(Cl)Cl>O.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]([CH2:9][C:10]([NH:19][C:18]1[CH:20]=[CH:21][C:15]([Cl:14])=[CH:16][CH:17]=1)=[O:12])[CH3:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 78124-ChloroanilineHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 21833458HCID 21833458, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of N-(tert-butoxycarbonyl)-N-methylglycine (10 g), 4-chloroaniline (8.8 g), benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent, 25.7 g) and methylene chloride (150 ml) is added dropwise triethylamine (5.9 g) while the temperature of the mixture is kept at 0-5° C. After addition, the mixture is stirred at room temperature for 8 hours, and thereto is added water. The methylene chloride layer is collected, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent; chloroform), and recrystallized from diethyl ether to give 2-[N'-(tert-butoxycarbonyl)-N'-methylamino]-N-(4-chlorophenyl)acetamide, m.p. 126-128° C.

Workup

  1. customis kept at 0-5° C
  2. additionAfter addition
  3. customThe methylene chloride layer is collected
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography (eluent; chloroform)
  7. customrecrystallized from diethyl ether

Sources & evidence

ORD record
ord-fdb6e9878f7c41539b0dd75c730fb21a
Source dataset
uspto-grants-1999_10
Patent number
US05972946

Reaction notes

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