Benzotrichloride → HCID 13685244, compound

HRID 2419533Notes

Reaction equation

HRID 2419533 reaction equation
Cl.[NH2:2][C:3]1[CH:9]=[C:8]([OH:10])[C:7]([NH2:11])=[CH:6][C:4]=1[OH:5].[C:12]1([C:18](Cl)(Cl)Cl)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[C:12]1([C:18]2[O:5][C:4]3[CH:6]=[C:7]4[N:11]=[C:18]([C:12]5[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=5)[O:10][C:8]4=[CH:9][C:3]=3[N:2]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 7367BenzotrichlorideHCID 20262798HCID 20262798, compound

Product 1

HCID 13685244HCID 13685244, compound

Conditions

Temperature
190 °C

Procedure

In the apparatus described in Example 13, 5.9 g of 2,5-diaminohydroquinone hydrochloride (28 m moles) were placed and at 180° C, 7.6 g of benzotrichloride (39 m moles) were added drop by drop. After 3 hours of heating at 190° C, the mixture was cooled and ground with mortar and pestle. The reaction product was extracted twice with 150 ml of xylene and passed through an aluminum oxide column heated at 125° C. The product was 4.5 g of crude XXII (74% of the theory). After two recrystallizations from xylene the melting point was 319°-323° C.

Workup

  1. customwere placed and at 180° C
  2. temperaturethe mixture was cooled
  3. extractionThe reaction product was extracted twice with 150 ml of xylene
  4. temperatureheated at 125° C
  5. customAfter two recrystallizations from xylene the melting point was 319°-323° C.

Sources & evidence

ORD record
ord-45715b09160d4562954798a7cff33a5d
Source dataset
uspto-grants-1978_08
Patent number
US04107169

Reaction notes

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