Hexane → HCID 20131008, compound

HRID 845364Notes

Reaction equation

HRID 845364 reaction equation
[Cl:1]N1C(=O)CCC1=O.[C:9]([C:13]1[CH:14]=[C:15]([CH:36]=[C:37]([C:40]([CH3:43])([CH3:42])[CH3:41])[C:38]=1[OH:39])[C:16]([O:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([NH:26][C:27](=[O:35])[CH2:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[CH:20]=1)=[O:17])([CH3:12])([CH3:11])[CH3:10].CCCCCC>C(Cl)(Cl)Cl>[C:40]([C:37]1[CH:36]=[C:15]([CH:14]=[C:13]([C:9]([CH3:10])([CH3:11])[CH3:12])[C:38]=1[OH:39])[C:16]([O:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([NH:26][C:27](=[O:35])[CH:28]([Cl:1])[C:29](=[O:34])[C:30]([CH3:31])([CH3:32])[CH3:33])[CH:20]=1)=[O:17])([CH3:43])([CH3:42])[CH3:41]

Participants

5

Reactant 3

HCID 8058HexaneHCID 31398ChlorosuccinimideHCID 20131006HCID 20131006, compound

Product 1

HCID 20131008HCID 20131008, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-chlorosuccinimide (16.3 g; 0.122 mole) was added with stirring to a solution of the compound (55.7 g; 0.1 mole) from (c) in chloroform (480 ml) and stirring continued for 18 hr. The volume of the mixture was reduced to approximately 100 ml and hexane (250 ml) added. The mixture was washed with water (2×100 ml) and the organic solution dried and evaporated to give a solid. This material was crystallized from dichloromethane (100 ml) and hexane (500 ml), to give the product (44.5 g; 83%) as a white solid, m.p. 185°-187° C.

Workup

  1. additionadded
  2. washThe mixture was washed with water (2×100 ml)
  3. customthe organic solution dried
  4. customevaporated
  5. customto give a solid
  6. customThis material was crystallized from dichloromethane (100 ml) and hexane (500 ml)
  7. customto give the product (44.5 g; 83%) as a white solid, m.p. 185°-187° C.

Sources & evidence

ORD record
ord-89395d2156174e12bf03787c0724f630
Source dataset
uspto-grants-1988_07
Patent number
US04758501

Reaction notes

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