Chloroacetyl chloride → HCID 13021162, compound

HRID 2058940

Reaction equation

HRID 2058940 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:6][CH:5]([CH3:7])[CH2:4][C:3]1=O.CC1CC(C)(C)CC1=O.S([O-])([O-])(=O)=O.[NH4+].[NH4+].C(N)C=C.ClCC(Cl)=O.C(N(CC)CC)C.C[C:43]1(C)CC(C)[C:45]([N:49](CC=C)[C:50](=[O:53])[CH2:51][Cl:52])=[CH:44]1.CC1CC(C)(C)C(N(CC=C)C(=O)CCl)=C1>C1C=CC=CC=1>[CH3:7][C:5]1[CH2:6][C:2]([CH3:9])([CH3:1])[CH2:3][C:4]=1[N:49]([CH2:45][CH:44]=[CH2:43])[C:50](=[O:53])[CH2:51][Cl:52]

Participants

10

Reactant 8

HCID 6577Chloroacetyl chlorideHCID 7853AllylamineHCID 8471TriethylamineHCID 1073242,4,4-TrimethylcyclopentanoneHCID 1196322,2,4-TrimethylcyclopentanoneHCID 6097028Ammonium SulfateHCID 13021160HCID 13021160, compoundHCID 13021161HCID 13021161, compound

Product 1

HCID 13021162HCID 13021162, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

By the same procedure as in Example 63 using a mixture comprising 2,2,4-trimethylcyclopentanone and 2,4,4-trimethylcyclopentanone (about 1:1) (25.2 parts by weight; 0.2 mole) in 0.2 liter of benzene, 0.1 part by weight of ammonium sulfate, and 11.4 parts by weight (0.2 mole) of allylamine, further reacted with 22.6 parts by weight (0.2 mole) of chloracetyl chloride in 0.05 liter of benzene and 22 parts by weight (0.2 mole) of triethylamine in 0.1 liter of benzene, a mixture of isomers consisting of N-(3,3,5-trimethylcyclopenten-1-yl)-N-allyl-α-chloroacetamide, N-(3,5,5-trimethylcyclopenten-1-yl)-N-allyl-α-chloroacetamide, and N-(2,4,4-trimethylcyclopenten-1-yl)-N-allyl-α-chloroacetamide was obtained. The yield of brown oily distillate (B.P.=88°-93° C. at 1.0 torr) having a refractive index (nD20 =1.4978) was 29 parts by weight. The content of organically combined chlorine was 15.9% (14.7%). The nitrogen content was 6.1% (5.8%).

Workup

  1. additiona mixture of isomers

Sources & evidence

ORD record
ord-dca8fee64b6548ecab7c62a651f09001
Source dataset
uspto-grants-1982_03
Patent number
US04319918

Linked notes

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