Acetic Anhydride → HCID 19761440, compound

HRID 249335Notes

Reaction equation

HRID 249335 reaction equation
[CH3:1][C:2]([CH3:23])([CH3:22])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14]1)=[O:4].CCN(CC)CC.[C:31](OC(=O)C)(=[O:33])[CH3:32]>C(Cl)Cl>[CH3:1][C:2]([CH3:23])([CH3:22])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]1[C:31](=[O:33])[CH3:32])=[O:4]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 19761400HCID 19761400, compound

Product 1

HCID 19761440HCID 19761440, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.38 g 2,2-dimethyl-N-[2-(2,3-dihydro-1H-indol-2-yl)-4-chlorophenyl]propanamide in 40 ml CH2Cl2 at 10° C. were added 12.7 ml Et3N and then dropwise 6.59 ml acetic anhydride. The resulting mixture was stirred twenty-four hours at room temperature. The reaction was quenched with water (30 ml). The organic phase was separated, washed with 5% HCl, water, 7.5% NaHCO3 and sat. NaCl (1×), and dried (MgSO4). Concentration, trituration with hexane and recrystallization from cyclohexane gave 2.10 g solid, m.p. 131°-134° C.

Workup

  1. customThe reaction was quenched with water (30 ml)
  2. customThe organic phase was separated
  3. washwashed with 5% HCl, water, 7.5% NaHCO3 and sat. NaCl (1×)
  4. dry with materialdried (MgSO4)
  5. concentrationConcentration, trituration
  6. customwith hexane and recrystallization from cyclohexane

Sources & evidence

ORD record
ord-98e98881be4547ddbbfedf6a45d2c207
Source dataset
uspto-grants-1993_05
Patent number
US05214059

Reaction notes

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