Cyanogen Bromide → 2,2-Dimethoxy-1-methylpropylcyanamide

HRID 615262Notes

Reaction equation

HRID 615262 reaction equation
[N:1]#[C:2]Br.[CH3:4][O:5][C:6]([O:11][CH3:12])([CH3:10])[CH:7]([NH2:9])[CH3:8]>O.CO>[CH3:4][O:5][C:6]([O:11][CH3:12])([CH3:10])[CH:7]([NH:9][C:2]#[N:1])[CH3:8]

Participants

5

Reactant 2

HCID 10476Cyanogen BromideHCID 158518261-Methyl-2,2-dimethoxypropylamine

Product 1

HCID 201644792,2-Dimethoxy-1-methylpropylcyanamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Cyanogen bromide (424 mg., 4 m moles) was added to a solution of 2,2-dimethoxy-1-methylpropylamine (266 mg., 2 m moles) and KHCO3 (400 mg., 4 m moles) in a mixture of water (2 ml.) and methanol (4 ml.). After 15 minutes the mixture was poured into water (150 ml.) and the mixture extracted with CH2Cl2. The extract was washed with water and brine, dried (MgSO4) and evaporated to dryness to give 2,2-dimethoxy-1-methylpropylcyanamide as a pale yellow oil (280 mg., 88%) having the following n.m.r. spectrum in CDCl3 : 1.15 (s, 3H), 1.18 (d, 3H); 3.15 (s, 6H); 3.0-3.6 (m, 1H); 4.0 (m, 1H).

Workup

  1. extractionthe mixture extracted with CH2Cl2
  2. washThe extract was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-b33e2376a4334f72a40abad4790fb097
Source dataset
uspto-grants-1985_02
Patent number
US04497949

Reaction notes

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