Dichloromethane → HCID 15406052, compound

HRID 2119258Notes

Reaction equation

HRID 2119258 reaction equation
ClCCl.[C:4]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29](O)=[O:30])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(OC(Cl)=O)C(C)C.[C:40](#[N:44])[CH2:41][C:42]#[N:43]>C(N(CC)CC)C>[C:4]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29](=[C:41]([C:40]#[N:44])[C:42]#[N:43])[OH:30])([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8010MalononitrileHCID 62365Isobutyl chloroformateHCID 5969746-(tritylamino)caproic acid

Product 1

HCID 15406052HCID 15406052, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a dichloromethane solution of 6-(tritylamino)-caproic acid (20.0 g, 53 mmole) and triethylamine (20 mL) in an ice bath was added dropwise over 30 min isobutylchloroformate (8.3 mL, 64 mmole). After the mixture was stirred for 2 hr in an ice bath, freshly distilled malononitrile (4.2 g, 64 mmole) was added all at once. The solution was stirred for 2 hr in an ice bath and for 2 hr at RT. The dichloromethane solution was washed with ice cold 2N HCl (300 mL) and the biphasic mixture was filtered to remove product that precipitated (13.2 g). The phases were separated and the organic layer dried and evaporated to a thick syrup. The syrup was covered with dichloromethane and on standing deposited fine crystals of product. The crystals were filtered and dried to give 6.3 g for a total yield of 19.5 g (87%) of the product, which is useful as an intermediate.

Workup

  1. stirringThe solution was stirred for 2 hr in an ice bath and for 2 hr at RT
  2. washThe dichloromethane solution was washed with ice cold 2N HCl (300 mL)
  3. filtrationthe biphasic mixture was filtered
  4. customto remove product that
  5. customprecipitated (13.2 g)
  6. customThe phases were separated
  7. customthe organic layer dried
  8. customevaporated to a thick syrup
  9. filtrationThe crystals were filtered
  10. customdried

Sources & evidence

ORD record
ord-77999a320a3c445b82dbc5ff7ef4fa9a
Source dataset
uspto-grants-2004_02
Patent number
USRE038416E1

Reaction notes

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