Isoamyl Nitrite → HCID 90418262, compound

HRID 2177305Notes

Reaction equation

HRID 2177305 reaction equation
CC(C)CC[N+]([O-])=O.N(OCCC(C)C)=O.[Br:17]Br.N[C:20]1[S:24][N:23]=[C:22]([C:25]([F:28])([F:27])[F:26])[C:21]=1[C:29]#[N:30]>C(Cl)Cl>[Br:17][C:20]1[S:24][N:23]=[C:22]([C:25]([F:28])([F:27])[F:26])[C:21]=1[C:29]#[N:30]

Participants

6

Reactant 4

HCID 8053Isoamyl NitriteHCID 24408BromineHCID 693963-Methyl-1-nitrobutaneHCID 69176628HCID 69176628, compound

Product 1

HCID 90418262HCID 90418262, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Into a 100-mL round-bottom flask, was placed 3-methyl-1-nitrobutane (14.4 g, 122.92 mmol, 6.00 equiv), isopentyl nitrite (30 mL), Br2 (32.4 g, 202.74 mmol, 10.00 equiv). This was followed by the addition of 5-amino-3-(trifluoromethyl)-1,2-thiazole-4-carbonitrile (4.0 g, 20.71 mmol, 1.00 equiv), in portions at 0° C. The resulting solution was stirred for 30 min at 0° C. in a water/ice bath. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:4). The resulting solution was diluted with 30 mL of DCM. The resulting mixture was washed with 2×50 mL of Na2SO3/H2O. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10). This resulted in 4.5 g (85%) of 5-bromo-3-(trifluoromethyl)-1,2-thiazole-4-carbonitrile as yellow crude oil.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. washThe resulting mixture was washed with 2×50 mL of Na2SO3/H2O
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. customThis resulted in 4.5 g (85%) of 5-bromo-3-(trifluoromethyl)-1,2-thiazole-4-carbonitrile as yellow crude oil

Sources & evidence

ORD record
ord-f8209a8cbcfe4404bcb1f112cefbacea
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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