Ammonia → HCID 20334397, compound

HRID 1706795Notes

Reaction equation

HRID 1706795 reaction equation
[OH-].[K+].N.[Br:4][C:5]1[CH:6]=[CH:7][C:8]2[NH:9][C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3.[NH2-].[Na+].Br[CH2:21][C:22]#[CH:23].[K+].[Br-]>>[CH2:23]([N:9]1[C:8]2[CH:7]=[CH:6][C:5]([Br:4])=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:22]#[CH:21]

Participants

7

Reactant 6

HCID 222Ammonia2×HCID 7842Propargyl bromideHCID 14797Potassium HydroxideHCID 24533Sodium amideHCID 2524463-BromocarbazoleHCID 253877Potassium Bromide

Product 1

HCID 20334397HCID 20334397, compoundYield 95%

Conditions

Temperature
-33 °C

Procedure

A 500 ml, three-necked, round bottom flask was fitted with mechanical stirrers, thermometer, Dry Ice/acetone reflex condenser (with KOH drying tube) and addition funnel. To the flask was added 210 ml of liquid ammonia and 8.7 g (0.035 mole) of 3-bromocarbazole (from Example 16A). To this mixture was added 1.52 g (0.039 mole) of sodium amide at -33° C. The resulting mixture was stirred mechanically at -33° C. for 3 hr. The mixture was then cooled to -55° C. and 5.9 g (0.049 mole) of 3-bromo-1-propyne was added dropwise over a period of 20 min. After stirring at -55° C. for an additional 5 hr, the ammonia was allowed to evaporate overnight. The residue was extracted three times with 300 ml portions of benzene. Concentration of the combined benzene extractants gave 9.5 g (95% yield) of light yellow powder, m.p. 142°-149° C. Recrystallization from methanol gave colorless needle crystals, m.p. 155°-157° C. I.R. (KBr pellet) in cm-1 : 3300 (C≡CH), 3070 (Ar--H), 2940 (CH), 2140 (C≡C), 1630+1600 (C=C), 1455+1330 (CN), 800+740+720 (Ar), 680+660 (C≡CH). Anal: calculated for C15H10NBr: C, 63.40%; H, 3.55%; N, 4.93%; found: 63.37%; H, 3.35%; N, 4.83%.

Workup

  1. customA 500 ml, three-necked, round bottom flask was fitted with mechanical stirrers
  2. temperatureThe mixture was then cooled to -55° C.
  3. stirringAfter stirring at -55° C. for an additional 5 hr
  4. customto evaporate overnight
  5. extractionThe residue was extracted three times with 300 ml portions of benzene
  6. customConcentration of the combined benzene extractants gave 9.5 g (95% yield) of light yellow powder, m.p. 142°-149° C
  7. customRecrystallization from methanol
  8. customgave colorless needle crystals, m.p. 155°-157° C

Sources & evidence

ORD record
ord-957cab67f05243c69076bd4b4b27eee7
Source dataset
uspto-grants-1980_06
Patent number
US04208501

Reaction notes

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