Acetic Anhydride → HCID 86664643, compound

HRID 2275479Notes

Reaction equation

HRID 2275479 reaction equation
[CH:1]1([NH:7][C:8](=[N:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[O:9][N:10]=[C:11]([CH3:13])[CH3:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:21]([N:14]([CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)[C:8](=[N:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[O:9][N:10]=[C:11]([CH3:13])[CH3:12])(=[O:23])[CH3:22]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 86664634HCID 86664634, compound

Product 1

HCID 86664643HCID 86664643, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 1,3-dicyclohexyl-O—(N-isopropylideneamino)-isourea (Cmpd. 3) (16.7 g, 60 mmol) and 4-dimethylaminopyridine (180 mg) in pyridine (40 ml) is added acetic anhydride (8.9 ml, 90 mmol). The mixture is stirred 2 h and then evaporated under reduced pressure. The residue is diluted with hexane (150 ml), washed with water (5×20 ml), dried over MgSO4 and evaporated. The solid residue is recrystallized from hexane to afford 13.3 g of the title compound as white crystals, mp 74-78° C.

Workup

  1. customevaporated under reduced pressure
  2. additionThe residue is diluted with hexane (150 ml)
  3. washwashed with water (5×20 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe solid residue is recrystallized from hexane

Sources & evidence

ORD record
ord-fb70db6726ec417e99d8a5b03feb5922
Source dataset
uspto-grants-2015_09
Patent number
US09127098B2

Reaction notes

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