Triethylamine → HCID 12761811, compound

HRID 1763903Notes

Reaction equation

HRID 1763903 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:6]=[C:5]([I:13])[C:4]=1[OH:14].[C:15](=[O:31])([O-])[O:16][C:17]1[CH:22]=C(Cl)C(Cl)=C(C(C)(C)C)[C:18]=1Cl.[CH2:32](N(CC)CC)C>O>[OH:14][C:4]1[C:5]([I:13])=[CH:6][C:7]([C:9]([CH3:11])([CH3:10])[CH3:12])=[CH:8][C:3]=1[CH2:2][NH:1][C:15](=[O:31])[O:16][C:17]([CH3:18])([CH3:22])[CH3:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1192862-Aminomethyl-4-t-butyl-6-iodophenolHCID 86585469HCID 86585469, compound

Product 1

HCID 12761811HCID 12761811, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 2-aminomethyl-4-(1,1-dimethylethyl)-6-iodophenol (12 g., 0.04 mole) in tetrahydrofuranwater (10:3; v:v; 130 ml.) is added 1,1-dimethylethyl-2,4,5-trichlorophenyl carbonate (13 g., 0.044 mole) and triethylamine (4.44 g., 0.044 mole). The resulting pale yellow solution is stirred and heated at 60°-65° C. for 24 hours, cooled to 20° C. and diluted with water (700 ml.). The solid which precipitates is collected, air-dried, triturated with petroleum ether and dried to give 1,1-dimethylethyl N-[2-hydroxy-3-iodo-5-(1,1-dimethylethyl)phenylmethyl]carbamate as a colorless solid (14.3 g., 88%), m.p. 196°-197° with dec. Recrystallization from ethyl acetate affords an analytical sample of 1,1-dimethylethyl N-[2-hydroxy-3-iodo-5-(1,1-dimethylethyl)phenylmethyl]carbamate as colorless crystals, m.p. 199°-200° with dec.

Workup

  1. temperatureheated at 60°-65° C. for 24 hours
  2. customThe solid which precipitates
  3. customis collected
  4. customair-dried
  5. customtriturated with petroleum ether
  6. customdried

Sources & evidence

ORD record
ord-ad7b2431712a48b0b285fc47c309778d
Source dataset
uspto-grants-1978_09
Patent number
US04113877

Reaction notes

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